In 2005, Levine wrote, produced, and directed his debut film Territory, based on his stage play of the same name. Critic Aaron West of eFilmCritic wrote of the film, "The off-Broadway version is undoubtedly the more appropriate medium for this story, and if given a choice, I would rather see it there. Still, I cannot help but applaud Levine for trying something a little different. His characters are extraordinarily ordinary, and his tightly wound screenplay reveals their (and our) brightest and darkest sides at various times."

In 2009, he wrote and directed the short films The Empress and Fat Friend.

His next film, 2010's romantic drama/comedy Gabi on the Roof in July, received a positive critical response and was praised by Eric Kohn of Indiewire, who called the film a "lightly amusing comedy". The film is also noteworthy for featuring an early appearance of Actress and filmmaker Lena Dunham.

Levine is married to fellow filmmaker Sophia Takal, with whom he has collaborated on several films. In 2013, Jordan Zakarin of The Hollywood Reporter named Levine and Takal two of New York's next big independent filmmakers.

In 2014, Levine wrote, directed, and starred in the mystery/comedy Wild Canaries. The film received a positive response from critics and was praised by The Village Voice as being "...the closest a contemporary film has come to replicating the unbridled jubilance of a classic screwball comedy".