In 1998, Levin directed the feature film, Slam, which won the Grand Jury Prize at the Sundance Film Festival, the Golden Camera Award at Cannes, and the Audience Choice Award at the St. Louis International Film Festival. He went on to direct the documentary, Thug Life in D.C. which earned him an Emmy in 1999 and documentary award nominations from the Directors Guild and the International Documentary Association.
Levin then directed Whiteboyz, nominated for the Grand Prix at the Paris Film Festival in 2000, as well as the Grand Special Prize at the Deauville Film Festival. In 2000, he directed the documentary, Soldiers in the Army of God, for which he won the Certificate of Merit at the San Francisco International Film Festival. In 2001, he won another nomination for the Grand Special Prize at the Deauville Film Festival for his feature film, Brooklyn Babylon. He has also directed the documentaries, The Last Party; Twilight: Los Angeles; Street Time; and The Protocols of Zion, a documentary about anti-semitism in the United States following the events of 9/11. Most recently, he directed the documentary, Mr. Untouchable, about the most powerful drug kingpin in New York City; Schmatta: Rags to Riches to Rags for HBO; the documentary series Brick City and episodes of Law & Order.