In 1998, Fischler starred in the independent film The Week That Girl Died, a romantic comedy about three long-time friends in a small New England fishing town. For the part, he received a best lead actor award by the American Film Institute International Film Festival's New Directions jury, which honors independent films. Fischler also appeared in David Lynch's 2001 psychological thriller Mulholland Drive as a man describing a horrible nightmare he had. He also appeared in the 2002 television film Gilda Radner: It's Always Something, a biopic about Comedian Gilda Radner, where he played the real-life Comedian Eugene Levy. He appeared in the films Twister (1996), Ghost World (2001), and Old School (2003). and The Great Buck Howard (2008), and played assistant district attorney Ellis Loew in Brian De Palma's 2006 crime film The Black Dahlia. The character was referred to in the film as "Jewboy", Film reviewer Stephen Cole called his role in that film "a caricature that is as coarsely anti-Semitic as any sequence in Mel Gibson’s The Passion of the Christ." Fischler also appeared as a guest star in television shows Angel, Nash Bridges, Burn Notice, Lie to Me, Bones, Cold Case, Monk, Star Trek: Enterprise, Girlfriends, CSI: Crime Scene Investigation, CSI: Miami and CSI: NY. By 2009, he had more than 60 film and television credits.