27, a fiction film in the guise of a documentary, follows an artist, a group of actors, a filmmaker, and students who share similar desires to be free, to try things, to love, and to be loved. James Leary, a young artist who has walked away from his success in New York invites filmmaker Marc Lafia to his studio to talk. The filmmaker constructs a series of narratives to amplify James' fears and ecstasies, juxtaposing his life with Lola, an early teen poet; Divina, an intellectual with whom he's in love and who wants to be free of him; and Tzuan, his Taiwanese student perplexed by translation; all this folding into the documentary and another film made by Alejandro, a theater director making a film with James, melding Shakespeare and surrealism.