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Tilly starred in Bound (1996), directed by The Wachowskis, which portrays a lesbian relationship her character has with Gina Gershon.She played Samantha Cole in the Jim Carrey comedy Liar Liar (1997).She is a semi-regular cast member on Family Guy, voicing the Griffin family's neighbor, Bonnie Swanson.
Her mother divorced again when Tilly was 16, and moved to Victoria, where Tilly attended Belmont High School.
She appeared as Garry's girlfriend on It's Garry Shandling's Show, which aired on Showtime.
She was also cast as a high-end prostitute on the short-lived comedy Key West, alongside Fisher Stevens.
Tilly is a World Series of Poker Ladies' Event bracelet winner, the first celebrity to win a World Series tournament. Tilly came to prominence when she received an Academy Award nomination for her portrayal of Olive Neal in Woody Allen's 1994 film Bullets over Broadway.
She earned further acclaim, as well as Saturn Award and MTV Award nominations, for her performance in the Wachowskis' 1996 neo-noir thriller Bound.