Clinton "Clint" Eastwood, Jr. (born May 31, 1930) is an American film actor, director, producer and composer. He has received five Academy Awards, five Golden Globe Awards, a Screen Actors Guild Award and five People's Choice Awards—including one for Favorite All-Time Motion Picture Star.

Eastwood is primarily known for his alienated, morally ambiguous, anti-hero acting roles in violent action and western films, particularly in the 1960s, 1970s and 1980s. Following his role on the long-running television series Rawhide, he went on to star as the Man With No Name in the Dollars trilogy of Spaghetti Westerns and as Inspector Harry Callahan in the Dirty Harry film series. These roles have made him an enduring icon of masculinity. Eastwood is also known for his comedic efforts in Every Which Way but Loose (1978) and Any Which Way You Can (1980), his two highest-grossing films after adjustment for inflation. For his work in the films Unforgiven (1992) and Million Dollar Baby (2004), Eastwood won Academy Awards for Best Director, producer of the Best Picture and received nominations for Best Actor. These films in particular, as well as others such as Play Misty for Me (1971), The Outlaw Josey Wales (1976), Escape from Alcatraz (1979), In the Line of Fire (1993), The Bridges of Madison County (1995) and Gran Torino (2008) have all received great critical acclaim and commercial success. He has directed most of his star vehicles as well as films he has not acted in, such as Mystic River (2003) and Letters from Iwo Jima (2006), for which he received Academy Award nominations. He also served as the non-partisan mayor of Carmel-by-the-Sea, California, from 1986–1988, tending to support small business interests on the one hand and environmental protection on the other.

Eastwood was born in San Francisco, California, to Clinton Eastwood Sr. (1906-1970), a steelworker and migrant worker, and Margaret Ruth Runner (1909-2006), a factory worker. He was a large baby (12 pounds and 6 ounces) and was named "Samson" by the nurses in the hospital. Eastwood has English, Scottish, Dutch and Irish ancestry and was raised in a "middle class Protestant home". His family moved often, as his father worked at different jobs along the West Coast. The family settled in Piedmont, California, where Eastwood attended Piedmont Junior High School and Piedmont Senior High School. Later he transferred to Oakland Technical High School, where the drama teachers encouraged him to take part in school plays, but was not interested.

After high school, Eastwood intended to enter Seattle University and major in music, but in 1950, during the Korean War, he was drafted into the U.S. Army. He was stationed at Fort Ord where his certificate as a lifeguard got him appointed as a life-saving and swimming instructor. He later moved down to Los Angeles and began a romance with a girl named Maggie Johnson and during this time he worked managing an apartment house in Beverly Hills by day (into which he then moved) and worked at a Signal Oil gas station by night. He signed up to study at Los Angeles City College and quickly became engaged to Maggie; they married shortly before Christmas 1953 in South Pasadena and honeymooned in Carmel.

According to the CBS press release for Rawhide, Universal (known then as Universal-International) film company happened to be shooting in Fort Ord and an enterprising assistant spotted Eastwood and invited him to meet the director. However, the key figure, according to his official biography was a man named Chuck Hill, who was stationed in Fort Ord and had contacts in Hollywood. While in Los Angeles, Hill had reacquainted with Eastwood and managed to succeed in sneaking Eastwood into a Universal studio and showed him to cameraman Irving Glassberg. Glassberg was impressed with his appearance and stature and believed him to be, "the sort of good looking young man that has traditionally done well in the movies". Glassberg arranged for director Arthur Lubin to meet Eastwood at the gas station where he was working in the evenings in Los Angeles. Lubin, like Glassberg was highly impressed and swiftly arranged for Eastwood's first audition. However he was a little less enthusiastic of his first audition, remarking, "He was quite amateurish. He didn't know which way to turn or which way to go or do anything". Neverless, he told Eastwood not to give up, and suggested he attend drama classes, and later arranged for an initial contract for Eastwood in April 1954 at $100 a week. Some people in Hollywood, including his wife Maggie, were suspicious of Lubin's intentions towards Eastwood; he was homosexual and maintained a close friendship with Eastwood in the years that followed. After signing, Eastwood was initially criticised for his speech and awkward manner; he was soft-spoken and in performing in front of people was cold, stiff and awkward. Fellow talent school actor John Saxon, described Eastwood as, "being like a kind of hayseed. Thin, rural, with a prominent Adam's Apple, very laconic and slow speechwise."

In May 1954, Eastwood made his first real audition, trying out for a part in Six Bridges to Cross, a film about the Brinks robbery that would mark the debut of actor Sal Mineo. Director Joseph Pevney was not impressed by his acting and rejected him for any role. Later he tried out for Brigadoon, The Constant Nymph, Bengal Brigade and The Seven Year Itch in May 1954, Sign of the Pagan (June), Smoke Signal (August) and Abbott and Costello Meet the Keystone Kops (September), all without success. Eastwood was eventually given a minor role by director Jack Arnold in the film Revenge of the Creature, a film set in the Amazon jungle, which was the sequel to The Creature from the Black Lagoon which had been released just months earlier. In September 1954, Eastwood worked for three weeks on Arthur Lubin's Lady Godiva of Coventry in which he donned a medieval costume, and then in February 1955, won a role playing "Jonesy", a sailor in Francis in the Navy and his salary was raised to $300 a week for the four weeks of shooting. He again appeared in a Jack Arnold film, Tarantula, with a small role as a squadron pilot, again uncredited. In May 1955, Eastwood put four hours work into the film Never Say Goodbye, in which he again plays a white coated technician uttering a single line and again had a minor uncredited role as a ranch hand (his first western film) in August 1955 with Law Man, also known as Stars in the Dust. He gained experience behind the set, watching productions and dubbing and editing sessions of other films at Universal Studios, notably the Montgomery Clift film A Place in the Sun. Universal presented him with his first TV role with a small television debut on NBC's Allen in Movieland on July 2, 1955, starring actors such as Tony Curtis and Benny Goodman. Although his records at Universal revealed his development, Universal terminated his contract on October 25, 1955, leaving Eastwood gutted and blaming casting director Robert Palmer, on whom he would exact revenge years later when Palmer came looking for employment at his Malpaso Company. Eastwood rejected him.

On the recommendation of Betty Jane Howarth, Eastwood soon joined new publicity representatives, the Marsh Agency, who had represented actors such as Adam West and Richard Long. Althought Eastwood's contract with Lubin had ended, he was important in landing Eastwood his biggest role to date; a featured role in the Ginger Rogers - Carol Channing western comedy, The First Travelling Saleslady. Eastwood played a recruitment officer for Teddy Roosevelt's Rough Riders. He would also play a pilot in another of Lubin's productions, Escapade in Japan and would make several TV appearances under Lubin even into the early 1960s. As Eastwood grew in success, he never spoke to Lubin again until 1992, shortly after winning his Oscar for Unforgiven, when Eastwood promised a lunch that never happened. Without the contract of Lubin in the meantime, however, Eastwood was struggling. He was advised by Irving Leonard financially and under his influence changed talent agencies in rapid succession, the Kumin-Olenick Agency in 1956, and Mitchell Gertz in 1957. He landed a small role as temperamental army officer for a segment of ABC's Reader's Digest series, broadcast in January 1956, and later that year, a motorcycle gang member on a Highway Patrol episode. In 1957, Eastwood played a cadet who becomes involved in a skiing search and rescue in the 'White Fury' installment of the West Point series. He also appeared in an episode of the prime time series Wagon Train and a suicidal gold prospector in Death Valley Days. In 1958 he played a Navy lieutenant in a segment of Navy Log and in early 1959 made a notable guest appearance as a cowardly villain, intent on marrying a rich girl for money, in Maverick.

Eastwood was credited for his roles in several more films. He auditioned for the film The Spirit of St. Louis, a Billy Wilder biopic about aviator Charles Lindbergh. He was rejected and the role in the end went to Jimmy Stewart who just put on makeup to make him look younger. He did however have a small part as an aviator in the French picture Lafayette Escadrille, and played an ex-renegade in the Confederacy in Ambush at Cimarron Pass, his biggest screen role to date opposite Scott Brady. His part was shot in nine days for Regal Films Inc. Out of frustration, he said after watching it at the premiere, "It was sooo bad. I just kept sinking lower and lower in my seat and just wanted to quit". Around the time the film was released Eastwood described himself as feeling "really depressed" and regards it as the lowest point in his career and a point when he seriously considered quitting the acting profession.

Eastwood learned from Bill Shiffrin that CBS were casting an hour-long Western series and arranged for a screen test. With screenwriter Charles Marquis Warren overlooking, Eastwood had to recite one of Henry Fonda's monologues from the William Wellman western, The Ox-Bow Incident in his audition. A week later, Shiffrin rang Eastwood and informed him he had won the part of Rowdy Yates in Rawhide. He had successfully beaten competition such as Bing Russell and had got the break he had been looking for. Filming began in Arizona in the summer of 1958. Although Eastwood was finally pleased with the direction of his career, he was not especially happy with the nature of his Rowdy Yates character. At this time, Eastwood was 30, and Rowdy was too young and too cloddish for Clint to feel comfortable with the part, privately describing Yates as "the idiot of the plains" It took just three weeks for Rawhide to reach the top 20 in the TV ratings and soon rescheduled the timeslot half an hour earlier from 7.30 -8.30 pm every Friday, guaranteeing more of a family audience. For several years it was a major success, and reached its peak as number 6 in the ratings between October 1960 and April 1961. However, success was not without its price. The Rawhide years were undoubtedly the most gruelling of his life, and at first, from July until April, they filmed six days a week for an average of twelve hours a day. Although it never won Emmy stature, Rawhide earned critical acclaim and won the American Heritage Award as the best Western series on TV and it was nominated several times for best episode by the Writer's and Director's Guilds. Eastwood received some criticism during this period and was considered too laid back and lazy by some directors who believed he relied on his looks and just didn't work hard enough. Eastwood appeared in a western comedy series Maverick, in which he fought James Garner in the "Duel at Sundown" episode. Although Rawhide continued to attract notable actors such as Lon Chaney Jr, Mary Astor , Ralph Bellamy, Burgess Meredith, Dean Martin and Barbara Stanwyck, by late 1963 Rawhide was beginning to decline in popularity and lacked freshness in the script and was scrapped by early 1966.

In late 1963, an offer was made to Eastwood's co-star Eric Fleming on Rawhide to star in an Italian made western (A Fistful of Dollars), originally named The Magnificent Stranger, to be directed in a remote region of Spain by a relative unknown at the time, Sergio Leone. However, the money was not much, and Fleming always set his sights high on Hollywood stardom, and rejected the offer immediately. A variety of actors, including Charles Bronson, Steve Reeves, Richard Harrison, Frank Wolfe, Henry Fonda, James Coburn and Ty Hardin were considered for the main part in the film. Harrison had suggested Clint Eastwood, whom he knew could play a cowboy convincingly. Harrison later said: "Maybe my greatest contribution to cinema was not doing Fistful of Dollars, and recommending Clint for the part." Through Irving Leonard, the offer was made to Eastwood, who saw it as an opportunity to escape Rawhide and the states and saw it as a paid vacation. He signed the contract for $15,000 in wages for eleven weeks work and which also threw in a bonus of a Mercedes automobile upon completion, and arrived in Rome in May 1964. Eastwood was instrumental in creating the Man With No Name character's distinctive visual style that would appear throughout the Dollars trilogy. He had brought with him the black jeans he had purchased from a shop on Hollywood Boulevard which he had bleached out and roughened up, the hat from a Santa Monica wardrobe firm, a leather bracelet and two Indian leather cases with dual serpents, and the trademark black cigars came from a Beverly Hills shop, though Eastwood himself is a non-smoker and hated the smell of cigar smoke. Leone decided to use them in the film and heavily emphasised the "look" of the mysterious stranger to appear in the film. Leone commented, "The truth is that I needed a mask more than an actor, and Eastwood at the time only had two facial expressions: one with the hat, and one without it." The first interiors for the film were shot at the Cinecittà studio on the outskirts of Rome, before quickly moving to a small village in Andalucia, Spain in an area which had also been used for filming Lawrence of Arabia (1962) just a few years earlier. A Fistful of Dollars would become a benchmark in the development of the spaghetti westerns, and Leone would successfully create a new icon of a western hero, depicting a more lawless and desolate world than in traditional westerns. The trilogy would also redefine the stereotypical American image of a western hero and cowboy, creating a character gunslinger and bounty hunter which was more of an anti hero than a hero and with a distinct moral ambiguity, unlike traditional heroes of western cinema in the United States such as John Wayne.

Leone hired Eastwood to star in his second film of what would become a trilogy, For a Few Dollars More (1965). Screenwriter Luciano Vincenzoni was brought in to write the script which he wrote in nine days; two bounty hunters (Eastwood and Lee Van Cleef) pursuing a drug-addicted criminal (Volontè), planning to rob an impregnable bank. For a Few Dollars More was shot in the spring and summer of 1965 and again interiors of the film were shot at the Cinecittà studio in Rome before they moved to Spain again. Screenwriter Vincenzoni was very important in bringing the films to the states, given that he was fluent in English and accompanied Leone to a cinema in Rome to show the new film after completion to United Artist executives Arthur Krim and Arnold Picker. He sold the rights to the film and the third film (which was yet to be written let alone made) in advance in the states for $900,000, advancing $500,000 up front and the right to half of the profits.

In January 1966, Eastwood met with producer Dino De Laurentiis in New York City and agreed to star in a non-Western five-part anthology production named Le streghe or The Witches opposite his wife, actress Silvana Mangano. Eastwood's nineteen minute installment only took a few days to shoot and was not met well with critics, who described it as "no other performance of his is quite so 'un-Clintlike' ", with the New York Times disparaging it as a "throwaway De Sica". Two months after his De Sica shoot, Eastwood began working on the third Dollars film, The Good, the Bad and the Ugly, in which he again played the mysterious Man With No Name character. Lee Van Cleef was brought in again to play a ruthless fortune seeker, while Eli Wallach, a character actor noted for his appearance in The Magnificent Seven (1960), was hired to play the cunning Mexican bandit "Tuco", although the role was originally written for Volontè, who passed on working with Leone again. The three become involved in a search for a buried cache of confederate gold buried in a cemetery by a man named Jackson, in hiding as Bill Carson. Eastwood was not initially pleased with the script and was concerned he might be upstaged by Wallach, and said to Leone, "In the first film I was alone. In the second, we were two. Here we are three. If it goes on this way, in the next one I will be starring with the American cavalry". Filming began at the Cinecittà studio in Rome again in mid-May 1966, including the opening scene between Clint and Wallach when The Man With No Name captures Tuco for the first time and sends him to jail. The production then moved on to Spain's plateau region near Burgos in the north, which would double for the extreme deep south of the United States, and again shot the western scenes in Almeria in the south. This time the production required more elaborate sets, including a town under cannon fire, an extensive prison camp and an American Civil War battlefield; and for the climax, several hundred Spanish soldiers were employed to build a cemetery with several thousand grave stones to resemble an ancient Roman circus.

The Dollars trilogy was not shown in the United States until 1967. A Fistful of Dollars opened in January, For a Few Dollars More in May and The Good, the Bad and the Ugly in December 1967. The trilogy was publicised as James Bond-type entertainment and all films were successful in American cinemas and turned Eastwood into a major film star in 1967, particularly the The Good, the Bad and the Ugly which eventually collected $8 million in rental earnings. However, upon release, all three were generally given bad reviews by critics (despite the select few American critics who had seen the films in Italy previously having a positive outlook) and marked the beginning of Eastwood's battle to win the respect of American film critics. 

Eastwood spent much of late 1966 and 1967 dubbing for the English-language version of the films and being interviewed, something which left him feeling angry and frustrated. Stardom brought more roles in the "tough guy" mold and Irving Leornard (who would later pass away at Christmas 1969) gave him a script to a new film, the American revisionist western Hang 'Em High, a cross between Rawhide and Leone's westerns, written by Mel Goldberg and produced by Leornard Freeman. Eastwood signed for the film with a salary of $400,000 and 25% of the net earnings to the film, playing the character of Cooper, a man accused by vigilantes of a cow baron's murder and lynched and left for dead and later seeks revenge. With the wealth generated by the Dollars trilogy, Leonard helped set up a new production company for Eastwood, Malpaso Productions, something he had long yearned for and was named after a river on Eastwood's property in Monterey County. Leonard became the company's president and arranged for Hang 'Em High to be a joint production with United Artists. Inger Stevens of The Farmer's Daughter fame was cast to play the role of Rachel Warren with a supporting cast which included Pat Hingle, Dennis Hopper, Ed Begley, Bruce Dern and James MacArthur. Filming began in June 1967 in the Las Cruces area of New Mexico, and additional scenes were shot at White Sands and in the interiors were shot in MGM studios. The film became a major success after release in July 1968 and with an opening day revenue of $5,241 in Baltimore alone, it became the biggest United Artists opening in history, exceeding all of the James Bond films at that time. It debuted at number five on Variety's weekly survey of top films and had made its money back within two weeks of screening. It was widely praised by critics including Arthur Winsten of the New York Post who described Hang 'Em High as "A Western of quality, courage, danger and excitement".

Meanwhile, before Hang 'Em High had been released, Eastwood had set to work on Coogan's Bluff, a project which saw him reunite with Universal Studios after an offer of $1 million, more than doubling his previous salary. Jennings Lang was responsible for the deal, a former agent of a director called Don Siegel, a Universal contract director who was invited to direct Eastwood's second major American film. Eastwood was not familiar with Siegel's work but Lang arranged for them to meet at Clint's residence in Carmel. Eastwood had now seen three of Siegel's earlier films and was impressed with his directing and the two became natural friends, forming a close partnership in the years that followed. The idea for Coogan's Bluff originated in early 1967 as a TV series and the first draft was drawn up by Herman Miller and Jack Laird, screenwriters for Rawhide. It is about a character called Sheriff Walt Coogan, a lonely deputy sheriff working in New York City. After Siegel and Eastwood had agreed to work together, Howard Rodman and three other writers were hired to devise a new script as the new team scouted for locations including New York and the Mojave Desert. However, Eastwood surprised the team one day by calling an abrupt meeting and professed that he strongly disliked the script, which by now had gone through seven drafts, preferring Herman Miller's original concept. This experience would also shape Eastwood's distaste for redrafting scripts in his later career. Eastwood and Siegel decided to hire a new writer, Dean Riesner, who had written for Siegel in the Henry Fonda TV film Stranger on the Run some years previously. Don Stroud was cast as the psychopathic criminal Coogan is chasing, Lee J. Cobb as the disagreeable New York City Police Department lieutenant, Susan Clark as a probation officer who falls for Coogan and Tisha Sterling playing the drug addicted lover of Don Stroud's character. Filming began in November 1967 even before the full script had been finalized. The film was controversial for its portrayal of violence, but it had launched a collaboration between Eastwood and Siegel that lasted more than ten years, and set the prototype for the macho hero that Eastwood would play in the Dirty Harry films.

Eastwood was paid $850,000 in 1968 for the war epic Where Eagles Dare opposite Richard Burton. However, Eastwood initially expressed that the script drawn up by Alistair Mclean was "terrible" and was "all exposition and complications". The film was about a World War II squad parachuting into a Gestapo stronghold in the mountains, reachable only by cable car, with Burton playing the squad's commander and Eastwood his right-hand man. He was also cast as Two-Face in the Batman television series, but the series was cancelled before he played the part.

In 1969, Eastwood branched out by starring in his only musical, Paint Your Wagon. He and fellow non-singer Lee Marvin played gold miners who share the same wife (played by Jean Seberg). Production for the film was plagued with bad weather and delays and the future of the director's career (Joshua Logan) was in doubt. It was extremely high budget for this period and eventually exceeded $20 million. Although the film received mixed reviews, it was nominated for the Golden Globe Award for Best Motion Picture – Musical or Comedy.

In 1970, Eastwood starred in the western, Two Mules for Sister Sara with Shirley MacLaine. The film, directed by Siegel, is a story about an American mercenary who gets mixed up with a whore disguised as a nun and aid a group of Juarista rebels during the puppet reign of Emperor Maximilian in Mexico. The film saw Eastwood embody the tall mysterious stranger once more, although the film was considerably less crude and more sardonic than those of Leone. The film, which took four months to shoot and cost around $4 million to make, received mixed reviews, and Roger Greenspun of the New York Times reported, I'm not sure it is a great movie, but it is very good and it stays and grows on the mind the way only movies of exceptional narrative intelligence do".

Later in 1970 he appeared in the World War II movie, Kelly's Heroes with Donald Sutherland and Telly Savalas. The film, which stars Eastwood as one of a group of Americans who steal a fortune in bullion from the Nazis, combined tough-guy action with offbeat humor. It was last non-Malpaso film that Clint agreed to appear in. The filming commenced in July 1969 and was shot on location in Yugoslavia and London. Directed by Brian G. Hutton, the film involved hundreds of extras and dangerous special effects. The climax to the film echoes that of his Dollars films when he advances in lockstep on a German tiger tank on the street of a small European town, with a Morricone-esque soundtrack by Lalo Schifrin. The film received mostly a positive reception and its anti-war sentiments were recognized. The film has a respectable 83% fresh rating on Rotten Tomatoes.

In the winter of 1969-70, Eastwood and Siegel began planning his next film, The Beguiled. Jennings Lang was inspired by the 1966 novel by Thomas Cullinan and in passing the book to Eastwood he was engrossed throughout the night in reading the tale of a wounded Union soldier held captive by the sexually repressed matron of a southern girls' school. This was the first of several films where Eastwood has agreed to storylines where he is the centre of female attention, including minors. The film, according to Siegel, deals with the themes of sex, violence and vengeance and was based around, "the basic desire of women to castrate men". The film later received major recognition in France and is considered one of Eastwood's finest works by the French. However, although the film reached number two on Variety's chart of top grossing films, it was poorly marketed and in the end grossed less than $1 million. According to Eastwood and Jennings Lang, the film, aside from being poorly publicized, flopped due to Clint being "emasculated in the film".

1971 proved to be a professional turning point in Eastwood's career. Before Irving Leonard had died, the last film they had discussed at Malpaso was to give Eastwood the artistic control that he desired and make his directorial debut in Play Misty for Me. The script was originally thought of by Jo Heims, about a jazz disc jockey named Dave (Eastwood) who has a casual affair with Evelyn (Jessica Walter), one of his listeners who had been calling the radio station repeatedly at night asking him to play her favourite song, Erroll Garner's Misty. When Dave ends their relationship the female fan becomes possessive and then violent, turning into a crazed murderess. Filming commenced in Monterey in September 1970, with Eastwood obtaining the rights to Misty after meeting Garner at the Concord Music Festival in 1970 and paying $2,000 for the use of the song The First Time Ever I Saw Your Face by Roberta Flack. The film was highly acclaimed by critics.

The script to Dirty Harry was originally written by Harry Julian and Rita M. Fink, a story about a hard-edged New York City police inspector Harry Callahan, determined to stop a psychotic killer by any means at his disposal. Dirty Harry is arguably Eastwood's most memorable character and the lines that Callahan utters when addressing a wounded bank robber are often cited amongst the most memorable in cinematic history. The film has been credited with inventing the "loose-cannon cop genre" that is imitated to this day. Eastwood's tough, no-nonsense portrayal of Dirty Harry touched a cultural nerve with many who were fed up with crime in the streets and at a time when there were prevalent reports of local and federal police committing atrocities and overstepping their authority by entrapment and obstruction of justice. After release in December 1971, Dirty Harry proved a phenonemal success which would go on to become Siegel's highest grossing film and the start of a series of films which is arguably Eastwood's signature role, with fans demanding more. Although a number of critics such as Jay Cocks of Time praised his performance as Dirty Harry, describing him as "giving his best performance so far, tense, tough, full of implicit identification with his character", the film was widely criticized and accused of fascism through Eastwood's portrayal of the ruthless cop. Feminists in particular were outraged by the film and at the Oscars for 1971 protested outside holding up banners which read messages such as "Dirty Harry is a Rotten Pig".

Eastwood next starred in the loner Western Joe Kidd, released in 1972. Originally called The Sinola Courthouse Raid, it was about a character inspired by Reies Lopez Tijerina, an ardent supporter of Robert F. Kennedy, known for storming a courthouse in Tierra Amarilla, New Mexico in an incident in June 1967, taking hostages and demanding that the Hispanic people be granted their ancestral lands back to them. Under the director's helm of John Sturges, who had directed acclaimed westerns such as The Magnificent Seven (1960), filming began in Old Tucson in November 1971, overlapping with another film production, John Huston's The Life and Times of Judge Roy Bean, which was just wrapping up shooting. Outdoor sequences to the film were shot near June Lake, east of theYosemite National Park. Eastwood was also far from in perfect health during the film and suffered symptoms that relayed the possibility of a bronchial infection and suffered several panic attacks, falsely reported in the media as him having an allergy to horses. Joe Kidd received a mixed reception.

1973 proved another benchmark to Eastwood when he directed his first western, High Plains Drifter. It involves the story of a tall, mysterious stranger arriving in a brooding Western town where the people share a guilty secret. They hire the stranger to defend the town against three felons soon to be released but fail to recognise that they once killed this stranger in a brutal whipping and that his reappearance is supernatural. The ghostly stranger forces the people to paint the town red and names it "Hell" and seeks revenge. Holes in the plot were filled in with black humor and allegory, influenced by Sergio Leone. The revisionist film received a mixed reception from critics but was a major box office success. A number of critics thought Eastwood's directing was as a derivative as it was expressive with Arthur Knight in Saturday Review remarking that Clint had "absorbed the approaches of Siegel and Leone and fused them with his own paranoid vision of society". 

Eastwood turned his attention towards a script written by Jo Heims about a love blossoming between a middle-aged man and a teenage girl, Breezy. During casting for the film, Eastwood met Sondra Locke for the first time, an actress who would play a major role in many of his films for the next ten years and an important figure in his life. However, Locke, who was 26 at this time was considered too old for the Breezy part and after much auditioning, a young dark-haired actress named Kay Lenz, who had recently appeared in American Graffiti, was cast. Filming for Breezy began in the November of 1972 in Los Angeles. With Surtees occupied elsewhere, Frank Stanley was brought in to shoot the picture, the first of four films he would shoot for Malpaso. The film was shot very quickly and efficiently and in the end went $1 million under budget and finished three days before schedule. The film was not a major critical or commerical success, it barely reached the Top 50 before disappearing and was only made available on video in 1998.

After the filming of Breezy had finished, Warner Brothers announced that Eastwood had agreed to reprise his role as Detective Harry Callahan in a sequel to Dirty Harry, running under the title, Vigilance but later changed to Magnum Force given its gun theme. Writer John Milius came up with a storyline in which a group of rogue young officers in the San Francisco Police Force systematically exterminate the city's worst criminals, portraying the idea that there are worse cops than Dirty Harry. Filming commenced in late April 1973, and during filming Eastwood encountered numerous disputes with director Ted Post, scarring their relationship for several years. Although the film was a major success after release, grossing $58.1 million dollars in the United States alone, a new record for Eastwood, it was not a critical success. New York Times critics such as Nora Sayre criticised the often contradictory moral themes of the film and Frank Rich believed it "was the same old stuff".

In 1974, Eastwood teamed with Jeff Bridges in the buddy action caper Thunderbolt and Lightfoot. The film is a road movie about an ex Korean War veteran turned bank robber Thunderbolt (Eastwood) who teams with a young con man drifter, Lightfoot (Bridges) who try to stay ahead of the vengeful ex-members of his gang (George Kennedy and Geoffrey Lewis) in the search for a cash deposit abandoned from an old heist. Shot in Great Falls area of Montana, filming for Thunderbolt and Lightfoot was shot between July and September 1973. On release in spring 1974, the film was praised for its offbeat comedy mixed with high suspense and tragedy and Eastwood's acting performance was noted by critics but was overshadowed by Jeff Bridges who stole the show in his performance as Lightfoot. When Bridges was nominated for an Academy Award for Best Supporting Actor, Eastwood was reportedly fuming at his own lack of Academy Award recognition. Despite critical acclaim, however, the film was only a modest success at the box office, earning $32.4 million. Eastwood was unhappy with the way that United Artists had produced the film and swore "he would never work for United Artists again", and the scheduled two film deal between Malpaso and UA was cancelled.

The The Eiger Sanction was based on a critically acclaimed spy novel by Trevanian. The rights to the film were bought by Universal as early as 1972, soon after the book was published, and was originally a Richard Zanuck and David Brown production. Paul Newman was intended to the role of Jonathan Hemlock (Eastwood), an assassin turned college art professor who decides to return to his former profession for one last sanction in return for a rare Picasso painting; he must climb the Eiger face in Switzerland and perform the deed under perilous conditions. After reading the script, Newman declined, because he believed the film was too violent. Mike Hoover, an Academy Award nominated professional mountaineer from Jackson, Wyoming, was hired to serve as a mountaineering cinematographer and technical adviser during the shoot. He taught Eastwood how to climb over some weeks of preparation in the summer of 1974 in Yosemite. Filming commenced in Grindelwald, Switzerland, on August 12, 1974 with an extensive team of professional climbing experts and advisers on board from America, England, Germany, Switzerland and Canada. Despite prior warnings of the perils of the Eiger, the filming crew suffered a number of accidents. A 27-year old English climber David Knowles, who was acting as body double and photographer was tragically killed during filming, with Hoover narrowly escaping. Eastwood continued to insist on doing all his own climbing and stunts, despite potentially being just seconds from instant death. Upon its release in May 1975, The Eiger Sanction was a a commercial failure, receiving only $23.8 million at the box office and was panned by most critics, with Joy Gould Boyum of the Wall Street Journal remarking that, "the film situates villainy in homosexuals, and physically disabled men". Eastwood blamed Universal Studios for the films poor promotion and turned his back on them, forming a long-lasting agreement with Warner Brothers through Frank Wells that would transcend over 35 years of cinema and remain intact to this day.

The story to The Outlaw Josey Wales was inspired by a 1972 novel by an apparent Native Indian uneducated writer Forrest Carter, originally titled Gone to Texas and later retitled The Rebel Outlaw:Josey Wales. Later it would be revealed that Forrest Carter's identity was fake, and that the real author was Asa Carter, a onetime racist and supporter of Ku Klux Klan school of politics. It would be a Western, and the lead character, Josey Wales, is a rebel southerner who refuses to surrender his arms after the American Civil War and is chased across the old southwest by a group of enforcers. The characters of Wales, the Cherokee chief, Navajo squaw and the old settler woman and her daughter all appeared in the novel. Director Philip Kaufman cast Chief Dan George, who had been nominated for an Academy Award for Supporting Actor in Little Big Man as the old Cherokee Lone Watie. Sondra Locke, also a previous Academy Award nominee was cast by Eastwood against Kaufman's wishes, as the daughter of the old settler woman, Laura Lee. This marked the beginning of a close relationship between Eastwood and Locke that would last six films and the beginning of a raging romance that would last into the late 1980s. The film also featured his real-life seven-year old son Kyle Eastwood. Principal photography for The Outlaw Josey Wales began in mid-October 1975. A rift between Eastwood and Kaufman developed during the filming and soon after filming moved to Kanab, Utah on October 24, 1975, Kaufman was notoriously fired under Eastwood's command by producer Bob Daley. The sacking caused an outrage amongst the Directors Guild of America and other important Hollywood executives and resulted in a fine, reported to be around $60,000 for the violation. It resulted in the Director's Guild passing new legislation which reserved the right to impose a major fine on a producer for discharging a director and replacing him with himself. From then on the film was directed by Eastwood himself with Daley second in command, but with Kaufman's planning already in place, the team were able to finish making the film efficiently. Upon release in August 1976, The Outlaw Josey Wales was widely acclaimed by critics. Many critics and viewers saw Eastwood's role as an iconic one, relating it with much of America's ancestral past and the destiny of the nation after the American Civil War. The film was pre-screened at the Sun Valley Center for the Arts and Humanities in Idaho in a six-day conference entitled, Western Movies: Myths and Images and attended by some two hundred esteemed film critics, academics and directors. The film would later appear in Time magazines Top 10 films of the year. Roger Ebert compared the nature and vulnerability of Eastwood's portrayal of Josey Wales with his Man With No Name character in his Dollars westerns and praised the atmosphere of the film. The film is seen by many as a Western masterpiece and has been awarded a 97% rating on the critical website Rotten Tomatoes.

After The Outlaw Josey Wales, Eastwood was offered the role of Benjamin L. Willard in Francis Coppola's Apocalypse Now but declined as he did not want to spend weeks in the Philippines shooting it. He was also offered the part of a platoon leader in Ted Post's Vietnam War film, Go Tell the Spartans. Eastwood refused the part and Burt Lancaster played the character instead. In the end it was decided to make a third Dirty Harry film. The script, devised by Stirling Silliphant had Harry up against a San Francisco Bay area Symbionese Liberation Army type group, which in real life had terrorized the area in 1974 with ruthless kidnappings and violence, and the film would end in a shoot out at the gang's hideout on Alcatraz island. Eastwood met Silliphant in a restaurant in Tiburon and instantly took a liking to the script, particularly the shoot out and the idea of Callahan having a woman as a police partner, his worst nightmare, a relationship which would gradually blossom during the course of the film and provide a backbone to the film's structure as they encounter different situations, from initial hatred to a fondess of each other and Callahan's genuine sorrow on her being shot in the finale. Kate Moore was originally proposed to play the part of the female cop, but in the end it went to Tyne Daly, who was given considerable leeway in the development of her character, although after seeing the film at the premiere was horrified by the extent of the violence. With James Fargo to direct, filming commenced in the San Francisco bay area in the summer of 1976. The film ended up considerably shorter than the previous Dirty Harry films, and was cut to 95 minutes. Upon release in the fall of 1976, The Enforcer was a major commercial success and grossed a total of $100 million, $60 million in the United States and easily became Eastwood's best selling film to date, earning more than some of his previous films combined. However, critically, Eastwood's performance was poorly received and was named "Worst Actor of the Year" by the Harvard Lampoon and the film was criticised for its level of violence. His performance in the third installment was overshadowed by positive reviews given to Daly in her convincing role as the strong-minded female cop.

In 1977, Eastwood directed and starred in The Gauntlet, in which he played a down-and-out cop who falls in love with a prostitute whom he's assigned to escort from Las Vegas to Phoenix in order for her to testify against the mob. Written by Dennis Shryack and Michal Butler, Steve McQueen and Barbra Streisand were originally cast as the film's stars. However, fighting between the two forced them to drop out of the project, with Eastwood and Locke replacing them. References to political corruption and organized crime were depicted in the film. Although a moderate hit with the viewing public, critics were mixed about the film, with many believing it was overly violent.

In 1978, Eastwood starred in Every Which Way But Loose an uncharacteristic, offbeat comedy role. Eastwood played Philo Beddoe, a trucker and brawler who roamed the American West, searching for a lost love, while accompanying his best brother/manager Orville and his petorangutan, Clyde. An orangutan named Manis was brought in to play Clyde, Geoffrey Lewis as the dimwitted Orville, Beverly D'Angelo as his girlfriend and Sondra Locke as Lynn Halsey-Taylor, the country and western bar room singer. Upon its release, the film was a surprising success and became Eastwood's most commercially successful film at the time and ranks high amongst those of his career to date, becoming the second-highest grossing film of the year. However, it was panned by the critics, with Variety commenting that, "This film is so awful it's almost as if Eastwood is using it to find out how far he can go - how bad a film he can associate himself with". David Ansen of Newsweek described the film as, "plotless junk heap of moronic gags, sour romance and fatuous fisticuffs."

In 1979, Eastwood starred in the fact-based movie Escape from Alcatraz, his last collaboration with Don Siegel. He portrayed prison escapee Frank Morris, who was sent to the tough prison Alcatraz in 1960, devised a meticulous plan to escape from "The Rock," and, in 1962, broke out with two other prisoners and entered San Francisco Bay.

In 1980, Eastwood played the main attraction in a traveling Wild West Show in Bronco Billy. His children Kyle and Alison had small roles as orphans in Bronco Billy. Later in 1980, he reprised his role in the sequel to Every Which Way But Loose entitled Any Which Way You Can. Despite bad reviews from critics, the sequel also became another box-office success and was among the top five highest-grossing films of the year.

In Honkytonk Man (1982) Eastwood directed and starred in Honkeytonk Man. The first part of the movie was filmed in Bird's Landing, California. However, the majority of this feature was filmed in and around Calaveras County, east of Stockton, California. Exterior scenes include Main Street, Mountain Ranch; Main Street, Sheepranch; and the Pioneer Hotel in Sheepranch. Extras were locally hired and many of the towns residents are seen in the movie and his son Kyle played his nephew. Honkytonk Man received critical acclaim, and has a score of 93% on Rotten Tomatoes.

In 1982, Eastwood directed, produced and starred in the Cold War-themed Firefox, based on a 1977 novel with the same name by Craig Thomas. Russian filming locations were not possible due to the Cold War, and the producers selected Vienna and other locations in Austria to simulate many of the Eurasian story locations. The film was shot on a $21 million budget.

The fourth Dirty Harry film Sudden Impact (1983), is widely considered to be the darkest, "dirtiest" and most violent film of the series. Also, it was the highest-grossing film of the franchise, making Eastwood a viable star for the 1980s. This would be the last time he starred in a film with frequent leading lady Sondra Locke. President Ronald Reagan referred to his famous "Go ahead, make my day." line in one of his speeches.

Eastwood's daughter Alison had a much bigger role as his daughter in the provocative thriller Tightrope (1984), in which Eastwood starred as a single-father cop lured by the promise of kinky sex. Complicating matters are his struggle to single-handedly raise two young daughters, a growing relationship with a tough rape prevention officer played by Geneviève Bujold, and the troubling thought that the killer shares his own sexual preferences (bondage, masochism, etc.).

Eastwood starred in the period comedy City Heat (1984) with Burt Reynolds. The film was released in North America in December 1984. The pairing of Eastwood and Reynolds in a Prohibition-era action-comedy.

He revisited the western genre directing and starring in Pale Rider (1985). This movie has plot similarities to the classic Western Shane (1953), including a final scene that shares similarities to the famous ending of Shane. The film also bears similarities to Eastwood's previous Man with No Name character, and his 1973 western High Plains Drifter. The title is a reference to the Four Horsemen of the Apocalypse, as the rider of a pale horse is Death. It was primarily filmed in the Boulder Mountains and the SNRA in central Idaho, just north of Sun Valley in late 1984. The opening credits scene featured the jagged Sawtooth Mountains south of Stanley. Train-station scenes were filmed in Tuolumne County, California, near Jamestown. Scenes of a more established Gold Rush town (in which Eastwood's character picks up his pistol at a Wells Fargo office) were filmed in the real Gold Rush town of Columbia, also in Tuolumne County, California. The film also featured Michael Moriarty, Carrie Snodgress, Christopher Penn, Richard Dysart, Sydney Penny, Richard Kiel, Doug McGrath and John Russell. Pale Rider, is the only Eastwood film to have clear religious overtones throughout - though several of his other films such as High Plains Drifter also make heavy use of spiritual and supernatural ideas and imagery. The film premiered at the Cannes Film Festival.

In 1986, Eastwood starred in the military drama Heartbreak Ridge (1986) and played a United States Marine Gunnery Sergeant. The film is about the 1983 U.S. invasion of Grenada, West Indies. A portion of the movie was filmed on the island itself. The title comes from the Battle of Heartbreak Ridge in the Korean War. The character played by Eastwood was awarded the Medal of Honor for his heroic actions there.

Eastwood's fifth and final Dirty Harry film, The Dead Pool (1988), was a commercial success, but was generally panned by critics. It co-starred Liam Neeson, Patricia Clarkson, and a young Jim Carrey.

Eastwood began working on smaller, more personal projects, first directing Bird (1988), a biopic starring Forest Whitaker as jazz musician Charlie "Bird" Parker, a genre of music that Eastwood has always been personally interested in. Eastwood received two Golden Globes—the Cecil B. DeMille Award for his lifelong contribution and the Best Director award for Bird, which also earned him a Golden Palm nomination at the Cannes Film Festival.

Carrey would later appear with Eastwood in the poorly received comedy Pink Cadillac (1989) alongside Bernadette Peters and Eastwood's future girlfriend Frances Fisher, with whom he has since appeared in two more films. The film is about a bounty hunter and a group of white supremacists chasing after an innocent woman who tries to outrun everyone in her husband's prized pink Cadillac. The film received generally poor reviews. Pink Cadillac grossed just $12,143,484. In contrast, the movie Eastwood made just prior to Pink Cadillac, the fifth Dirty Harry movie, The Dead Pool, grossed $37,903,295.

In 1990 he starred as a character closely based on the legendary film-maker John Huston in White Hunter, Black Heart, an adaptation of Peter Viertel's roman à clef about the making of the classic The African Queen. The film was shot on location in Zimbabwe. Some interiors were shot in and around Pinewood Studios in England. The small steamboat they used in the whitewater scene is the same boat Humphrey Bogart's character captained in The African Queen (1951). It received some critical attention but only had a limited release. Later in 1990, Eastwood directed and co-starred with Charlie Sheen in The Rookie, a buddy cop action film. Raul Julia and Sonia Braga play German villains engaged in an illegal luxury car theft operation. The film features an unconventional female-on-male rape scene.

Eastwood rose to prominence yet again in the early 1990s, which would prove another benchmark in his career. In 1992, he revisited the western genre in the self-directed film, Unforgiven, taking on the role of an aging ex-gunfighter long past his prime. The film, also starring such esteemed actors as Gene Hackman, Morgan Freeman, and Richard Harris, laid the groundwork for such later westerns as Deadwood by re-envisioning established genre conventions in a more ambiguous and unromantic light. A great success both in terms of box office and critical acclaim, it was nominated for nine Academy Awards, including Best Actor for Eastwood and Best Original Screenplay for David Webb Peoples. It won four, including Best Picture and Best Director for Eastwood. As of 2009, Unforgiven is the last western film that Eastwood has made.

In 1993, Eastwood played Frank Horrigan, a guilt-ridden Secret Service agent in the thriller In the Line of Fire, co-starring John Malkovich and Rene Russo and directed by Wolfgang Petersen. As of 2009, it is his last acting role in a film he did not direct himself. This film was a blockbuster and among the top 10 box-office performers in that year. Later in 1993, Eastwood directed and co-starred with Kevin Costner in A Perfect World. It grossed $31 million in box office receipts in the United States with overseas gross at $101 million, making it a financial success. The film received largely positive reviews, with an 85% score on Rotten Tomatoes. In the years since its release, the film has been acclaimed by critics as one of Eastwood's most underrated directorial achievements. Cahiers du cinéma selected A Perfect World as the best film of 1993.

Eastwood continued to expand his repertoire by playing opposite Meryl Streep in the love story The Bridges of Madison County (1995). Based on a best-selling novel, it was also a hit at the box-office and grossed $182 million.

Eastwood directed and starred in the well-received political thriller Absolute Power. The film's ensemble cast featured Gene Hackman, Ed Harris, Laura Linney, Scott Glenn, Dennis Haysbert, Judy Davis, and E.G. Marshall. Eastwood played a veteran thief who witnesses the Secret Service cover up a murder the President was responsible for.

Eastwood directed Midnight in the Garden of Good and Evil, which starred John Cusack, Kevin Spacey and Jude Law. In 1999, Eastwood directed True Crime. Clint Eastwood plays Steve Everett, a journalist recovering from alcoholism, given the task of covering the execution of murderer Frank Beechum (played by Isaiah Washington). Everett discovers that Beechum might be innocent, but has only a few hours to prove his theory and save Beechum's life. The film was a large box-office bomb domestically. It had an opening weekend gross of $5,276,109 in the US and grossed $16,649,768 total in the US, out of a budget of $55 million. It received mixed reactions from critics, with a score of 51% on Rotten Tomatoes.

In 2000, Eastwood directed and starred in Space Cowboys, which also starred Tommy Lee Jones, Donald Sutherland, and James Garner. In the film, he plays Frank Corvin, a retired NASA engineer called upon to save a dying Russian satellite. The film was also one of the year's commercial hits.

In 2002, Eastwood played an ex-FBI agent on the track of a sadistic killer in Blood Work, which was derived from a book by Michael Connelly. Blood Work is loosely based on the 1998 novel by the same name from Edgar Award-winning writer Michael Connelly. Eastwood won the Future Film Festival Digital Award at the Venice Film Festival.

Eastwood directed the crime drama Mystic River about murder, vigilantism, and sexual abuse. The film featured Sean Penn, Kevin Bacon, Tim Robbins and Laurence Fishburne. The film was a commercial success and won two Academy Awards, as well as nominations for Best Director and Best Picture.

In 2005, Eastwood found critical and commercial success when he directed, produced, scored, and starred in the boxing drama Million Dollar Baby. Eastwood played a cantankerous trainer who forms a bond with the female boxer (Hilary Swank) he reluctantly trains after being persuaded by his lifelong friend (Morgan Freeman). The film won the Academy Award for Best Picture, as well as earning Eastwood a Best Actor nomination and a win for Best Director. Swank and Freeman also won Oscars for their performances, and the trio was nominated for the Screen Actors Guild Award for Outstanding Performance by a Cast in a Motion Picture. Eastwood also received a Grammy nomination for the score he composed for the film. Million Dollar Baby was in theaters from late January to early June 2005, grossed more than $216 million at the box office and was his highest-grossing film at the time.

In 2006, Eastwood directed two films about the battle of Iwo Jima in World War II. The first one, Flags of Our Fathers, focused on the men who raised the American flag on top of Mount Suribachi. The second one, Letters from Iwo Jima, dealt with the tactics of the Japanese soldiers on the island and the letters they wrote to family members. Both films were highly praised by critics and garnered several Oscar nominations, including Best Director and Best Picture for Letters from Iwo Jima.

In 2008, Eastwood directed the Oscar-nominated drama Changeling, which starred Angelina Jolie. Later that year, he ended his "self-imposed acting hiatus" with Gran Torino. Eastwood directed, starred, held a producer role, and co-wrote the theme song for the film. It grossed close to $30 million during its wide-release opening weekend in January 2009, making Eastwood, at age 78, the oldest leading man to reach #1 at the box office. Gran Torino grossed over $268 million worldwide in theaters and is the highest-grossing film of Eastwood's career so far without adjustment for inflation. Eastwood has said that this will most likely be the last time he acts in a movie.

In 2009, Eastwood directed the movie Invictus, with Morgan Freeman as Nelson Mandela and Matt Damon as rugby team captain Francois Pienaar. Carlin sold the film rights to Morgan Freeman. Eastwood and Warner Bros. have purchased the film rights to James R. Hansen's First Man: The Life of Neil A. Armstrong, the authorized biography of astronaut Neil Armstrong. No production date has been announced. As of September 2009, he is in talks to direct Peter Morgan's Hereafter for Warner Bros. Eastwood had announced that he has all but retired from acting, although maintained that "if a good western script turns up, you never know..." Eastwood currently donates funds toward the new CSUMB campus library. In early 2007, Eastwood announced that he will produce a Bruce Ricker documentary about jazz legend Dave Brubeck. The film is tentatively titled Dave Brubeck – In His Own Sweet Way. It will trace the development of Brubeck's latest composition, the Cannery Row Suite. This work was commissioned by the Monterey Jazz Festival and premiered at the 2006 festival. Eastwood's film crews captured early rehearsals, sound checks, and the final performance. Ricker and Eastwood are currently working on a documentary about Tony Bennett, as well, titled The Music Never Ends.

Hereafter is a forthcoming thriller film directed by Eastwood from a screenplay by Peter Morgan. It stars Matt Damon as "a reluctant psychic", and co-stars Cécile de France, and Lyndsey Marshal. Filming commenced in France on October 19, 2009. A days filming was done at the old Belle Epoque hotel in the village of Planet, near Chamonix which was transformed into a Swiss hospital for scenes between Cécile de France and Marthe Keller. Production then moved to Paris for four days and on October 21 a short scene between de France and Mylène Jampanoï was filmed in a stairwell inside the France Télévisions building. In the first week of November, production moved to London, England, for three weeks of filming in locations including Bermondsey and in Walworth. Scenes were also filmed on the Heygate Estate. Filming resumed on January 12, 2010; Eastwood filmed scenes with de France for three days on the Hawaiian island of Maui. Production next moved to the San Francisco Bay Area. On January 19, scenes featuring Damon were shot at the California and Hawaiian Sugar Company refinery in Crockett, California, which represents a flour mill on screen. Production returns to London on January 29 to shoot the final scenes with Damon. Variety has described the script as a thriller" in the vein of The Sixth Sense." Peter Morgan told The Hollywood Reporter, "It's quite spiritual material, and quite romantic, too. It's the sort of piece that's not easy to describe and in the hands of different filmmakers could end up as wildly different films. Quite unlike some of my other material, which I think there were only certain ways that you could shoot it."

Eastwood has had a strong passion for music since a young age, particularly a love of jazz, and he also is a country and western enthusiast. He dabbled in music early on and in late 1959 had produced the album Cowboy Favorites which was released on the Cameo label. The album included some classics such as Bob Wills's San Antonio Rose and Cole Porter's Don't Fence Me In and despite his attempts to plug the album by going on a tour, it never reached the Billboard Hot 100. Later in 1963, Cameo producer Kal Mann would bluntly tell him that "he would never make it big as a singer". Nevertheless, during the off season of filming Rawhide, Eastwood and Brinegar, sometimes joined by Sheb Wooley would go on touring rodeos, state fairs and festivals and in 1962 their act entitled Amusement Business Cavalcade of Fairs earned them as much as $15,000 a performance.

Eastwood has his own Warner Bros. Records-distributed imprint, Malpaso Records, as part of his deal with Warner Bros. This deal was unchanged when Warner Music Group was sold by Time Warner to private investors. Malpaso has released all of the scores of Eastwood's films from The Bridges of Madison County onward. It also released the album of a 1996 jazz concert he hosted, titled Eastwood after Hours — Live at Carnegie Hall.

Eastwood had tried for some time to direct an episode of Rawhide, even being promised at one point the possibility of doing so. However, because of differences between the president of the studio and show producers, Eastwood's opportunity fell through. In 1985, he made his only foray into TV direction to date with the Amazing Stories episode Vanessa In The Garden, starring Harvey Keitel and Sondra Locke; this was his first collaboration with writer/executive producer Steven Spielberg (Spielberg later produced A Perfect World, Flags of Our Fathers, and Letters from Iwo Jima). Eastwood has chosen a wide variety of films to direct, some clearly commercial, others highly personal. Eastwood produces many of his films, and is well known in the industry for his efficient, low-cost approach to making films; he has said that "everything I do as a director is based upon what I prefer as an actor." Over the years, he has developed relationships with many other filmmakers, working over and over with the same crew, production designers, cinematographers, editors, and other technical people. Similarly, he has a long-term relationship with the Warner Bros. studio, which finances and releases most of his films. However, in a 2004 interview appearing in The New York Times, Eastwood noted that he still sometimes has difficulty convincing the studio to back his films. In the 2000s, Eastwood also began composing music for some of his films. He is one of the subjects profiled in the documentary Fog City Mavericks, which interviews Eastwood alongside other fellow San Francisco Bay Area filmmakers such as George Lucas and Francis Ford Coppola. As producer, director, and actor, Eastwood has worked exclusively with legendary film poster designer Bill Gold. Gold designed (and often photographed) posters for 35 Clint Eastwood films, from Dirty Harry (1971) to Million Dollar Baby (2004).

Eastwood registered as a Republican in order to vote for Dwight D. Eisenhower in 1952 and he supported Richard Nixon's 1968 and 1972 presidential campaigns, but later criticized Nixon's morality during Watergate (see the February 1974 edition of Playboy). He usually describes himself as a libertarian in interviews, fiscally conservative yet socially liberal. At times, he has supported Democrats in California, such as the liberal and environmentally-concerned Representative Sam Farr in 2002. Indeed, Eastwood contributed $1,000 to Farr's successful re-election campaign that year and on May 23, 2003, the iconic actor-director hosted a $5,000-per-ticket fundraiser for California's Democratic governor, Gray Davis. Later that year, Eastwood offered to film a commercial in support of California's embattled governor, while in 2001, the star visited Davis' office to support an alternative energy bill written by another Democrat, California State Assemblyman Fred Keeley. In general, Eastwood has favored less governmental interference in both the private economy and the private lives of individuals. He has disapproved of a reliance on welfare, instead feeling that government should help citizens make something of themselves via education and incentive. He has, however, approved of unemployment insurance, bail-outs for homeowners saddled with unaffordable mortgages, a continued American automobile industry, electric and hybrid cars, free prescription drugs, government-ordained educational standards, environmental conservation, land preservation, alternative energy, and moderate gun control measures such as California's Brady Bill. A longtime liberal on civil rights, Eastwood has stated that he has always been pro-choice on abortion. He has also endorsed the notion of marriage equality (i.e. allowing gays to marry), just as he had once contributed to groups supporting the Equal Rights Amendment for women. Eastwood disapproved of America's wars in Korea (1950–1953), Vietnam (1964–1973), and Iraq (2003–present), believing that the U.S. should not be overly militaristic or playing the role of global policeman. In all, he considers himself too individualistic to be either right-wing or left-wing, having sometimes described himself as a "political nothing" and a "moderate". Eastwood has also stated that he doesn't see himself as conservative, but that he isn't "ultra-leftist," either. Eastwood made one successful foray into elected politics, becoming the Mayor of Carmel-by-the-Sea, California (population 4,000), a wealthy small town and artist community on the Monterey Peninsula, for one term. During his tenure, he completed Heartbreak Ridge and Bird. In 2001, he was appointed to the California State Park and Recreation Commission by Democratic Governor Gray Davis. He was reappointed in 2004 by Governor Arnold Schwarzenegger, whom he supported in the elections of 2003 and 2006 (although Eastwood disapproved of the recall of Davis in 2003). Soon afterwards Governor Schwarzenegger announced a proposal to close 80 percent of California State Parks. Eastwood, the vice chairman of the commission, and commission chairman, Bobby Shriver, Schwarzenegger's brother-in-law, led a California State Park and Recreation Commission panel in its unanimous opposition in 2005 to a six-lane, 16-mile (26 km), toll road that would cut through San Onofre State Beach, north of San Diego, and one of Southern California's most cherished surfing beaches. Eastwood and Shriver also supported a 2006 lawsuit to block the toll road and urged the California Coastal Commission to reject the project, which it did in February 2008. In March 2008, Eastwood and Shriver, whose terms had expired, were not reappointed. The Natural Resources Defense Council (NRDC) asked for a legislative investigation into the decision to not re-appoint Eastwood and Shriver, citing their opposition to the toll road extension. According to the NRDC and The New Republic, Eastwood and Shriver were not reappointed again in 2008 because both Eastwood and Shriver opposed the freeway extension of California State Route 241, that would cut through the San Onofre State Beach. This extension is likewise supported by Governor Schwarzenegger. Schwarzenegger's press release appointing Alice Huffman and Lindy DeKoven to replace Eastwood and Shriver makes no mention of a reason for the commission change. Governor Schwarzenegger appointed Eastwood (along with actor and director Danny DeVito, actor and director Bill Duke, producer Tom Werner and producer and director Lili Zanuck) to the California Film Commission in April 2004. During the 2008 United States Presidential Election, Eastwood endorsed John McCain for President, citing the fact that he had known McCain since 1973. He donated $2,300 towards McCain's campaign funds. Although sympathetic towards her bid for the presidency, Eastwood expressed disappointment with Hillary Clinton for engaging in a duck-hunting photo op, saying, "I was thinking: 'The poor duck, what the hell did she do that for?' I don't go for hunting. I just don't like killing creatures. Unless they're trying to kill me. Then that would be fine." Upon the election of Barack Obama, Eastwood stated "Obama is my president now and I am going to be wishing him the very best because it is what is best for all of us."

Eastwood told biographer Richard Schickel that he lost his virginity at age 14. He has fathered at least seven children by five different women. Biographer Patrick McGilligan claims Eastwood also fathered a child who was given up for adoption and several others that were aborted. According to McGilligan and biographer Marc Eliot, Eastwood always had a strong sexual appetite and had affairs with tens of women through the years, including many of his co-stars such as Inger Stevens (Hang 'Em High), Jean Seberg (Paint Your Wagon), Jo Ann Harris (The Beguiled), Kay Lenz (Breezy), actresses Peggy Lipton and Rebecca Pearle, Jane Brolin, and swimming champion Anita Lhoest . He also had an affair with French actress Catherine Deneuve, while in Paris in the mid 1960s. Biographer Patrick McGilligan and friend Paul Lippman have claimed that Eastwood was particularly sexually active and promiscuous in the 1970s and that he used his apartment close to the Hog's Breath Inn which he purchased in Carmel in the early 1970s to meet young ladies for "nooners" and "five in the afternooners". According to Lippman, "Eastwood seemed to get a bang out of this kinkier side to himself and rarely concealed it, often gloated about it".

Eastwood married swimsuit model Maggie Johnson on December 19, 1953, six months after they met on a blind date. Eastwood originally did not want to have children with his wife, then she became ill with hepatitis. After she recovered, he changed his mind, and Johnson became pregnant after fourteen years of marriage. They had two children: Kyle Eastwood (born May 19, 1968) and Alison Eastwood (born May 22, 1972). They separated around 1975, but Johnson did not take any legal action until 1978, when she filed for a legal separation. Eastwood was ordered to pay her $25 million ($1 million for each year they were married). Their divorce, however, was not finalized until May 1984. During his marriage to Johnson, Eastwood had an affair with Roxanne Tunis, who was an extra on Rawhide during the late 1950s and early 1960s. They had a daughter, Kimber Eastwood, born on June 17, 1964. Over the years, Eastwood financially supported Tunis and their daughter, and would secretly visit them every three to four months, according to Kimber. Kimber's son, Clinton, was born on February 21, 1984. The existence of Eastwood's love child and secret grandchild were unknown to the public and even Eastwood's family until reported by the National Enquirer in 1989. Since then Kimber has had a small role in her father's film Absolute Power. Eastwood had a fourteen-year relationship with actress Sondra Locke, whom he met in 1972 and co-starred in six films: The Outlaw Josey Wales, The Gauntlet, Every Which Way but Loose, Bronco Billy, Any Which Way You Can, and Sudden Impact. Locke became pregnant by Eastwood twice, and had two abortions and a tubal ligation. Their relationship ended acrimoniously in 1989. She filed a palimonysuit against Eastwood, and the litigation continued for a decade, with Locke suing him a second time for fraud. Locke and Eastwood finally resolved the dispute with a non-public settlement in 1999. During his cohabitation with Locke, Eastwood had an affair with flight attendant Jacklyn Reeves, with whom he had a son, Scott, and a daughter, Kathryn. The fact that Scott and Kathryn Reeves were the actor's children was not publicly known until a Carmel reporter revealed the information in the 1990s. Since then, the son (now known as Scott Eastwood) has grown close to his father and has also become an actor. After breaking up with Locke, Eastwood moved in with Frances Fisher, whom he met in 1988 while filming Pink Cadillac. They appeared together in Unforgiven, and had a daughter, Francesca Fisher-Eastwood, born on August 7, 1993. Fisher moved out of their shared home in 1995 but remains friendly with Eastwood and later appeared with him in True Crime. Eastwood married anchorwoman Dina Ruiz on March 31, 1996, in Las Vegas when Eastwood surprised her with a private ceremony at a home on the Shadow Creek Golf Course. She is 35 years his junior. Kyle Eastwood served best man. The couple's daughter, Morgan Eastwood, was born on December 12, 1996.

Speaking in 2008 of his fatherhood in his late 70s, Eastwood said: "I'm a much better father now than when I was younger because then I was working all around the world and I was desperate to find the brass ring, so I worked constantly. Now my daughter takes precedence over everything and, even though I've done a lot of work in the past year, I haven't ignored her and have been involved in her school activities. I go to all the softball games and look ridiculous out there because almost everybody's got a much younger father than she does. But it's fun. I think you appreciate everything a lot more when you get to my age. I never started out thinking I would have a big family. But now, it's very important to me, and family relationships take precedence over work."