"The Wind Cried Larry" is a dark, comedic journey into the world of Oskar Zukowski, a twenty-something, socially-awkward would-be philosopher and filmmaker who lives in the dingy basement of the now-otherwise empty Detroit home where he grew up. Consumed with obscure philosophies of solitude and the meaninglessness of art, Oskar is making "The Eleventh Hour of a Man with One Friend," a film about the spiritual death of his seemingly imaginary girlfriend. A film, Oskar claims, that is going to change everything!
In order to bring his visions to reality, however, Oskar will have to abandon the safe world of his imagination and open himself up emotionally to the realities of the world around him.
Help comes in the form of Vincenzo Collachi, a passionate ex-adult film director from Italy, who shares Oskar’s obscure "beauty of the moment" anti-Hollywood philosophies on filmmaking, and appears to be on the run from Johnny Law. The film is set against backdrop of an urban art college set to host the second annual Wind Cried Larry Traveling Film and Video Festival.