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Silverman guest-starred in a second-season episode of the USA cable program Monk as Marci Maven.She returned in the sixth-season premiere and for the 100th episode.She also starred in the HBO sketch comedy series Mr.Show (1995–1997) and had the leading role for the 1997 independent film Who's the Caboose?Liam Lynch directed the film, which was distributed by Roadside Attractions.
She appeared in three episodes of Larry Sanders during its final two seasons., Silverman parodied sketches from Chappelle's Show, replaying Dave Chappelle's characterizations of Rick James and "Tyrone" as well as a Donnell Rawlings character based on the miniseries Roots.In 2006, Silverman placed 50th on Maxim Hot 100 List. Silverman was nominated for a Primetime Emmy Award In June 2007, she hosted the MTV Movie Awards.to show Jimmy Kimmel, her boyfriend at the time, a special video.The video turned out to be a song called "I'm Fucking Matt Damon" in which she and Matt Damon sang a duet about having an affair behind Kimmel's back.
The video created an "instant You Tube sensation." She won an Primetime Emmy Award for Outstanding Original Music and Lyrics at the 60th Primetime Emmy Awards.