Mikhail Lvovich Astrov is the Uncle Vanya's philosopher, marked by Chekhov's characteristically extended, brooding, and introspective speeches that appear to proceed with little reference to those around the speaker. Overworked and ruined by provincial life, Astrov finds himself numb to the world, unable to want and love, and dejected at the thought that he will be forgotten in the course of time. As Astrov's feelings are in some sense anesthetized by his empty and disappointing life, one perhaps finds Astrov's double in the dead patient he mentions a number of times, a man who died while under chloroform.

In terms of the plot, Astrov's missed chance at something like love is the failed seduction of Yelena. Though their affair might offer an escape from their respective miseries, it does not come to fruition and, instead, ends with a nostalgic farewell. Thus the two seem to experience a loss they cannot even be certain that they suffered, a potential loss, and look toward future regret. Moreover, we should qualify that this seduction does not show Astrov in love: he is merely fascinated by Yelena's beauty.

Astrov also serves as the play's visionary. In his plans of forest conservation he dreams of a legacy that he can leave for future generations, extols the beauty of nature, and pitches man's capacity to create over and against his impulse to destroy. On the other hand, one wonders if these visions are little more than drunken illusions: as Astrov will note in Act II, it is only when drunk that he feels "monumental" rather than "eccentric."

This convergence of attributes indeed makes Astrov a strange figure—not only to the boxed-in lifestyle of the provinces but to himself as well. Throughout the play, Astrov will appear in relation to the motif of self- estrangement, his sense of alienation from himself providing the occasion for his self-conscious ruminations.