Peet's first screen performances were in a television commercial for Skittles and an uncredited appearance as the girlfriend of the titular character in the second episode of The Larry Sanders Show in 1992. Her film debut was in the drama Animal Room (1995), which also starred Neil Patrick Harris and Matthew Lillard. She appeared in the November 1995 episode "Hot Pursuit" of Law and Order. For much of the late 1990s, Peet maintained a steady acting career in relatively obscure independent films co-starring more established actors. In 1996, for instance, she appeared in One Fine Day, with George Clooney and Michelle Pfeiffer, and She's the One, with Jennifer Aniston and Cameron Diaz. Peet appeared in the critically acclimed film Playing by Heart (1998), as part of an ensemble cast that included Sean Connery, Gillian Anderson, and Ryan Phillippe. She had her first major role as Jacqueline Barrett in the WB network series Jack & Jill, which aired for two seasons, between 1999 and 2001, to moderate success. She appeared in the eighth-season finale of Seinfeld ("The Summer of George") as a waitress whom Jerry Seinfeld meets. In 1999, Peet also starred in the fantasy romantic comedy Simply Irresistible, opposite Sarah Michelle Gellar. That film was panned by critics and flopped at the box office.