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Lehmann attended Columbia University. His first job in the film industry was answering phones at Francis Ford Coppola's American Zoetrope film company. Later he supervised cameras on films that included 1983's The Outsiders. Lehmann attended film school at USC and graduated in 1985. While at USC he made a student film, Beaver Gets a Boner, the title of which he believes helped get the attention of film executives who would later hire him.

Lehmann is probably most noted for directing the black comedy Heathers. He also directed 40 Days and 40 Nights, The Truth About Cats & Dogs, Hudson Hawk, Meet the Applegates, Airheads and Because I Said So.

Lehmann also directs for television, and has worked on the short lived HBO comedy series The Comeback and NBC's The West Wing. Lehmann has guest directed on The Larry Sanders Show, Watching Ellie and Century City. Recently, Lehmann has directed episodes of HBO dramas, Big Love and True Blood, as well as Showtime's Californication.

Lehmann's upcoming films include Your Word Against Mine.

At a Q & A session during 2007's South by Southwest film festival in Austin, Texas, Lehmann claimed he would never make a sequel to Heathers. He claimed Winona Ryder wanted to do Heathers set in Washington, D.C., but he saw no potential for the project.