Kleist was born into the von Kleist family in Frankfurt an der Oder in the Margraviate of Brandenburg. After a scanty education, he entered the Prussian Army in 1792, served in the Rhine campaign of 1796, and retired from the service in 1799 with the rank of lieutenant. He studied law and philosophy at the Viadrina University and in 1800 received a subordinate post in the Ministry of Finance at Berlin.

In the following year, Kleist's roving, restless spirit got the better of him, and procuring a lengthened leave of absence he visited Paris and then settled in Switzerland. Here he found congenial friends in Heinrich Zschokke and Ludwig Friedrich August Wieland (d. 1819), son of the poet Christoph Martin Wieland; and to them he read his first drama, a gloomy tragedy, The Schroffenstein Family (1803, originally entitled The Ghonorez Family).

In the autumn of 1802, Kleist returned to Germany; he visited Goethe, Schiller, and Wieland in Weimar, stayed for a while in Leipzig and Dresden, again proceeded to Paris, and returning in 1804 to his post in Berlin was transferred to the Domänenkammer (department for the administration of crown lands) at Königsberg. On a journey to Dresden in 1807, Kleist was arrested by the French as a spy; he remained a close prisoner of the France at Châlons - sur - Marne. On regaining his liberty, he proceeded to Dresden, where, in conjunction with Adam Heinrich Müller (1779 – 1829), he published the journal Phöbus in 1808.

In 1809 Kleist went to Prague, and ultimately settled in Berlin, where he edited (1810 / 1811) the Berliner Abendblätter. Captivated by the intellectual and musical accomplishments of the terminally ill Henriette Vogel, Kleist, who was himself more disheartened and embittered than ever, agreed to do her bidding and die with her, carrying out this resolution by first shooting Vogel and then himself on the shore of the Kleiner Wannsee (Little Wannsee) near Potsdam, on 21 November 1811.

According to the Encyclopædia Britannica Eleventh Edition, "Kleist's whole life was filled by a restless striving after ideal and illusory happiness, and this is largely reflected in his work. He was by far the most important North German dramatist of the Romantic movement, and no other of the Romanticists approaches him in the energy with which he expresses patriotic indignation."

In the spring of 1799, the 21 year old Kleist wrote a letter to his half - sister Ulrike in which he found it "incomprehensible how a human being can live without a plan for his life" (Lebensplan). In effect, Kleist sought and discovered an overwhelming sense of security by looking to the future with a definitive plan for his life. It brought him happiness and assured him of confidence, especially knowing that life without a plan only saw despair and discomfort. The irony of his later suicide has been the fodder of his critics.

His first tragedy, The Schroffenstein Family (Die Familie Schroffenstein), has been already referred to; the material for the second, Penthesilea (1808), queen of the Amazons, is taken from a Greek source and presents a picture of wild passion. More successful than either of these was his romantic play, Käthchen of Heilbronn (Das Käthchen von Heilbronn) (1808), a poetic drama full of medieval bustle and mystery, which has retained its popularity.

In comedy, Kleist made a name with The Broken Jug (Der zerbrochne Krug) (1808), while Amphitryon (1808), an adaptation of Molière's comedy, is of less importance. Of Kleist's other dramas, Die Hermannsschlacht (1809) is a dramatic work of anti - Napoleonic propaganda, written as Austria and France went to war. It has been described by Carl Schmitt as the "greatest partisan work of all time". In it he gives vent to his hatred of his country's oppressors. This, together with the drama The Prince of Homburg (Prinz Friedrich von Homburg oder die Schlacht bei Fehrbellin), which is among his best works, was first published by Ludwig Tieck in Kleist's Hinterlassene Schriften (1821). Robert Guiskard, a drama conceived on a grand plan, was left a fragment.

Kleist was also a master in the art of narrative, and of his Gesammelte Erzählungen (Collected Short Stories) (1810 – 1811), Michael Kohlhaas, in which the famous Brandenburg horse dealer in Martin Luther's day is immortalized, is one of the best German stories of its time. The Earthquake in Chile (Das Erdbeben in Chili) and St. Cecilia, or the Power of Music (Die heilige Cäcilie oder die Gewalt der Musik) are also fine examples of Kleist's story telling as is The Marquise of O (Die Marquise von O.). His short narratives have largely influenced Kafka's. He also wrote patriotic lyrics in the context of the Napoleonic Wars.

Apparently a Romantic by context, predilection, and temperament, Kleist subverts clichéd ideas of Romantic longing and themes of nature and innocence and irony, instead taking up subjective emotion and contextual paradox to show individuals in moments of crises and doubt, with both tragic and comic outcomes, but as often as not his dramatic and narrative situations end without resolution.

Seen as a precursor to Henrik Ibsen and modern drama because of his attention to the real and detailed causes of characters’ emotional crises, he was also understood as a nationalist poet in the German context of the early twentieth century, and was instrumentalized by Nazi scholars and critics as a kind of proto - Nazi author. To this day, many scholars see his play Die Hermannsschlacht ("The Battle of the Teutoburg Forest", 1808) as prefiguring the subordination of the individual to the service of the Volk (nation) that became a principle of fascist ideology in the twentieth century. Kleist criticism of the last generation has repudiated nationalist criticism and concentrated instead mainly on psychological, structural and post - structural, philosophical, and narratological modes of reading.

Kleist wrote one of the lasting comedies and most staged plays of the German canon, The Broken Jug (1803 – 05) in which a provincial judge gradually and inadvertently shows himself to have committed the crime under investigation. In the enigmatic drama The Prince of Homburg (1811), a young officer struggles with conflicting impulses of romantic self - actualization and obedience to military discipline. Prince Friedrich, who had expected to be executed for his successful but unauthorized initiative in battle, is surprised to receive a laurel wreath from Princess Natalie. To his question, whether this is a dream, the regimental commander Kottwitz replies, "A dream, what else?"

Kleist wrote his eight novellas later in his life and they show his radically original prose style, which is at the same time careful and detailed, almost bureaucratic, but also full of grotesque, ironic illusions and various sexual, political, and philosophical references. His prose often concentrates on minute details that then serve to subvert the narrative and the narrator, and throw the whole process of narration into question. In Betrothal in St. Domingo (Die Verlobung in Santo Domingo) (1811) Kleist examines the themes of ethics, loyalty, and love in the context of the colonial rebellion in Haiti of 1803, driving the story with the expected forbidden love affair between a young white man and a black rebel woman, though the reader's expectations are confounded in typically Kleistian fashion, since the man is not really French and the woman is not really black. Here for the first time in German literature Kleist addresses the politics of a race based colonial order and shows, through a careful exploration of a kind of politics of color (black, white, and intermediate shades), the self - deception and ultimate impossibility of existence in a world of absolutes.

Kleist is also famous for his essays on subjects of aesthetics and psychology which, to the closer look, show an unfathomable insight into the metaphysical questions discussed by philosophers of his time, such as Kant, Fichte and Schelling.

In the first of his larger essays, "On the gradual development of thoughts in the process of speaking", Kleist shows the conflict of thought and feeling in the soul of man, leading to unforeseeable results through incidents which in their turn provoke the inner forces of the soul to express themselves in a spontaneous flow of ideas and words, both stimulating one another to further development. Kleist's view of the hidden forces in the human soul and the quite unstable and endangered position of the mind in their struggle can be compared to Freud's psychoanalytic model of the soul, especially to his notion of the "unconscious" and its hidden influences on the ego.

Kleist claims that most people are advised to speak only about what they already understand. Instead of talking about what you already know, Kleist admonishes his readers to speak to others with "the sensible intention of instructing yourself." Fostering a dialogue through the art of "skillful questioning" is the key behind achieving a rational or enlightened state of mind. And yet, Kleist employs the example of the French Revolution as the climactic event of the Enlightenment era whereby man broke free from his dark and feudal chains in favor of liberty, equality, fraternity. It is not that easy though for Kleist. Man cannot simply guide himself into the future with a rational mind as his primary tool. Therefore, Kleist strongly advocates for the usefulness of reflection ex post facto or after the fact. In doing so, man will be able to mold his collective consciousness in a manner conducive to the principles of free will. By reflecting after the fact, man will avoid the seemingly detestable inhibitions offered in rational thought. In other words, the will to power has "its splendid source in the feelings," and thus, man must overcome his "struggle with Fate" with a balanced mixture of wisdom and passion.

The metaphysical theory in and behind Kleist's first essay is that consciousness, man's ability to reflect, is the expression of a fall out of nature's harmony, which may either lead to disfunction, when the flow of feelings is interrupted or blocked by thought, or to the stimulation of ideas, when the flow of feelings is cooperating or struggling with thought. A state of total harmony, however, cannot be reached. Only in total harmony of thought and feeling life and consciousness would come to be identical through the total insight of the mind, an idea elaborated and ironically presented in Kleist's second essay "The Puppet Theater" or "On the Marionette Theater" (Über das Marionettentheater).

In a simulated dialogue, Kleist has one of the interlocutors comment that marionettes possess a grace humans do not, a view which contradicts all aesthetic concepts of the past. Our consciousness and capacity for reflection cause us to doubt ourselves or become self conscious, and prevent us from acting with the single mindedness and purity of an animal or a puppet. And yet, consciousness is the effect of eating from the tree of knowledge, and we cannot escape it, as long as we are barred from Eden. The interlocutor suggests that the only way out of this dilemma would be to go all the way through, because the garden of Eden could possibly be open on the other side: if we continue to become more intelligent, wiser, and more self - aware, we may eventually be able to carry out the actions we choose, with the same confidence and harmony as a marionette dancing on the strings of a puppeteer. Consciousness creates a split in our nature, rendering us neither animals nor gods. The ultimate development of humankind would be to bring these two parts of ourselves into harmony and no longer suffer doubt or internal conflict. The ending of the essay might seem hopeful, but it leaves the question open as to whether this kind of perfection will ever be possible. It is difficult to determine Kleist's intentions or personal view, because the two interlocutors in the dialogue are obviously presented in an ironic way. Rather than a serious proposal of Kleist's ideas it seems more like an ironic play on the vain ideals of classicism and romanticism.

This essay also shows Fichte's influence on Kleist. Similar to Kleist, Fichte had emphasized man's ability and necessity to develop his mind in infinity, without ever being able to reach identity with the absolute, because the individual's existence just hangs on the difference.

Without Kleist saying this expressly, works of art, such as his own, may offer an artificial image of this ideal, though this is in itself wrenched out from the same sinful state of insufficiency and rupture that it wants to transcend.

Kleist's philosophy is the ironic rebuff of all theories of human perfection, whether this perfection is projected in a golden age at the beginníng (Hölderlin, Novalis), in the present (Hegel), or in the future (as the philosophers of the enlightenment and still Marx would have seen it). His essays show man, like the literary works, torn apart by conflicting forces and held together on the surface only by illusions, like that of real love (if this was not the worst of all illusions). Jeronimo, for example, in Kleist's The Earthquake in Chile, is presented as emotionally and socially repressed and incapable of self - control, but still clinging to religious ideas and hopes. At the end of a process marked by chance, luck and coincidence, and driven by greed, hatred and the lust for power, embodied in a repressive social order, the human being that at the beginning had been standing between execution and suicide, is murdered by a mob of brutalized maniacs who mistake their hatred for religious feelings.

The ending of this novella could be used to describe Kleist's concept of life as well as his philosophy and aesthetics, expressed in the ironic style which fits the content: "And sometimes ... it almost seemed to him, that he ought to be happy."

His Gesammelte Schriften were published by Ludwig Tieck (3 vols. 1826) and by Julian Schmidt (new ed. 1874); also by Franz Muncker (4 vols. 1882); by Theophil Zolling (4 vols. 1885); by K. Siegen, (4 vols. 1895); and in a critical edition by Erich Schmidt (5 vols. 1904 – 1905). His Ausgewählte Dramen were published by K. Siegen (Leipzig, 1877); and his letters were first published by Eduard von Bülow, Heinrich von Kleists Leben und Briefe (1848).