Her first major role was as "Jack" in the 1999 WB network series Jack & Jill (which aired for two seasons). She also appeared in the eighth-season finale of Seinfeld ("The Summer of George") as a waitress whom Jerry Seinfeld meets.
Her character is notable for seemingly dating two men at once: Jerry and her apparent roommate ("dude"), Lyle. Peet's first role in a widely-released feature film came in 2000, with The Whole Nine Yards, which, together with the cult film Whipped, helped to elevate her status from supporting actress to lead.
That same year, she was voted one of the 50 Most Beautiful People in the World by People magazine. Peet was also in the movie Saving Silverman with Jack Black and Steve Zahn.
She also starred in Something's Gotta Give in 2003, playing Diane Keaton's daughter, and, at one point, Jack Nicholson's girlfriend.
In 2005, Peet appeared in the play This Is How It Goes, filling in for Marisa Tomei at the last minute after six days of rehearsal.
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