Lehmann began his Hollywood career working for Francis Ford Coppola at Zoetrope Studios, supervising video cameras on "One From the Heart" (1982) and "The Outsiders" (1983). He returned to film school at USC where he directed the acclaimed short film "The Beaver Gets a Boner". Lehmann also provided a short, "Ed's Secret Life", for NBC's "Saturday Night Live". The success of these shorts led to a production deal with New World Pictures and his first feature directing assignment, "Heathers" (1989). Working from Daniel Waters' sardonic script, Lehmann fashioned a black comedy that dealt with high school cliques, teen alienation, suicide and murder. "Heathers" greatly improved the career standings of its leads, Winona Ryder and Christian Slater, and future "bad girl" Shannen Doherty (who was featured as one of the eponymous princesses) .
"Meet the Applegates" (1991) was Lehmann's second independent feature, with a script co-written with Redbeard Simmons. A moderately amusing film inspired by 1950s sci-fi B-movies, "Meet the Applegates" followed the adventures of a family of giant beetles from a South American rainforest who pose as humans to sabotage a nuclear power plant. The environmental message of the picture overwhelmed it and the result was mixed critical attention and lackluster box office receipts.
Lehmann's first studio-backed feature was to be a small, skewed view of a standard caper film, but through overproduction, it became one of the most critically reviled features in Hollywood history -- "Hudson Hawk" (1991). Based on a story by star Bruce Willis, it was intended to be a tongue-in-cheek Americanization of James Bond. Lehmann called in his "Heathers" screenwriter, Daniel Waters, to help beef up the script, but reportedly control of the film was seized by Willis and producer Joel Silver who were riding high based on the success of the "Die Hard" franchise. The result was a confused mishmash of styles with no substance. Lehmann was exonerated from blame as behind-the-scenes stories of Willis' undermining with Silver's backing emerged.
Lehmann tried to rebound with "The Good Son" about a 12 year old with murderous tendencies. After spending months in pre-production, developing the material and casting a relatively unknown young actor in the lead, the chairman of the studio informed Lehmann he had to cast actor Macaulay Culkin, reportedly because Culkin's father wouldn't allow his son to appear in the sequel to "Home Alone" unless he also played "The Good Son". Rather than give up his directorial control, Lehmann left the project and retreated to TV. He helmed episodes of the HBO comedy series "The Larry Sanders Show" and an acclaimed outing of "Homicide" (NBC, 1993). After a three year absence, Lehmann returned to features with the mild comedy "Airheads" (1994) that depicted a trio of wannabe rock stars who inadvertently become embroiled in a hostage situation at a Los Angeles radio station. While it provided a few laughs, the overall result was generally disappointing. Lehmann claimed that for contractual reasons he was forced to make compromises in his vision of the film. He found critical success but dismal box office with his first producing effort, the biopic of quirky film director "Ed Wood" (also 1994).
Lehmann received critical kudos for the "Good Housekeeping" segment of the Showtime series "Fallen Angels" (1995). In a bid for commercial success, Lehmann directed the romantic comedy "The Truth About Cats and Dogs" (1996) starring Uma Thurman and Janeane Garofalo as two rivals who team up to win the affections of newcomer Ben Chaplin.