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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. Her other film appearances include Let It Ride; The Fabulous Baker Boys (1989); Made in America (1993); The Getaway (1994); Edie & Pen; House Arrest (1996); Liar Liar (1997); Music from Another Room (1998); Stuart Little (1999); Dancing at the Blue Iguana (2000); The Cat's Meow; Monsters, Inc. (2001); The Haunted Mansion (2003); Home on the Range (2004); and Terry Gilliam's Tideland (2005). She is also known for providing the voice of Bonnie Swanson on the animated television series Family Guy (1999–present).

Tilly was the recipient of a Theatre World Award in 1993 for her performance in the Off-Broadway play One Shoe Off. Her other stage credits include the Broadway revivals of The Women (2001) and Don't Dress for Dinner (2012).