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In 2000, she portrayed Abbie Hoffman's wife Anita Hoffman opposite Vincent D'Onofrio as Hoffman in Steal This Movie!
, involving the couple's political activism during the Vietnam War era.
Dreaming of earning a slot on the writing staff of the TV show Late Night with David Letterman, she became a professional standup comedian upon graduating from college with degrees in History and American Studies.
Garofalo did an HBO Comedy Half-Hour special in 1995, among similar subsequent appearances, including a one-hour stand-up special in June 2010 entitled "If You Will," performed at Seattle's Moore Theatre, that aired on Epix in June 2010 and was released on DVD in September 2010.
Garofalo began her career as a stand-up comedian and became a cast member on The Ben Stiller Show, The Larry Sanders Show, and Saturday Night Live, then appeared in more than 50 movies, with leading or major roles in The Truth About Cats and Dogs, Wet Hot American Summer, The Matchmaker, Reality Bites, Steal This Movie!Garofalo's first movie role, filmed the year before she appeared on national television, was a brief comical appearance as a counter worker in a burger joint in Late for Dinner in 1991, but her real breakthrough into film came in Reality Bites (1994) as Winona Ryder's character's Gap-managing best friend Vickie.The role helped solidify Garofalo's status as a Generation X icon.Later that same year, she received second billing under Jerry Stiller in a comedic film about a low-budget movie producer entitled The Independent.
The following year, Garofalo was top-billed in Wet Hot American Summer, the 2001 cult comedy about an American summer camp, and starred in The Search for John Gissing., Clay Pigeons, Sweethearts, Mystery Men, and The Independent, among numerous others.