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, 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.

Silverman played a therapist in a skit for a bonus DVD of the album Lullabies to Paralyze by the band Queens of the Stone Age.

Silverman also appears at the end of the video for American glam metal band Steel Panther's "Death To All But Metal." On Jimmy Kimmel Live!

Show and VIP, and starred in films, including Who's the Caboose?

(1997), School of Rock (2003), Wreck-It Ralph (2012), A Million Ways to Die in the West (2014), and Ralph Breaks the Internet (2018).

, about a pair of New York comedians (Silverman and director Sam Seder) going to Los Angeles during pilot season to try to get a part in a television series; the film features numerous young comedians in supporting roles but never received a widespread theatrical release.

Silverman and Seder later made a six-episode television series sequel entitled Pilot Season in which Silverman stars as the same character and Seder again directed.

Instead, she performed stand-up comedy in Greenwich Village.

After beginning her stand-up career in 1992, Silverman was part of the 1993–94 season of Saturday Night Live (SNL) for 18 weeks as a writer and featured player. Only one of the sketches she wrote survived to dress rehearsal and none aired, although she did appear on the show as a cast member in skits, usually in smaller supporting roles.

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.

to show Jimmy Kimmel, her boyfriend at the time, a special video.

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