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Watch Jon Stewart’s 5 Greatest Daily Show Moments

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There are many notable moments from Jon Stewart’s 16 year reign at the helm of The Daily Show, following his evolution from a comedian to a genuine voice in critiquing media and politics. With Stewart’s last show set for Thursday, here are his top five moments from a long run—including one that took place off The Daily Show set.

The 9/11 Monologue

Stewart vs. Jim Cramer

Stewart shoots down Crossfire

Stewart schools Glenn Beck

Indecision 2000

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See Jon Stewart's Career Over the Years

THE DAILY SHOW, 1996-present, Jon Stewart 1999-present
Jon Stewart takes the reins as anchor of The Daily Show in 1999.Comedy Central/Everett
Stewart gets a cameo as Kevin Gerrity in the 1999 Adam Sandler movie Big Daddy.Columbia
The Tonight Show with Jay Leno - Season 9
Jay Leno interviews Jon Stewart on The Tonight Show With Jay Leno in 2000.NBC/Getty Images
MCDDETO EC011
Stewart plays Marion Frank Stokes in the 2002 black comedy Death to SmoochyWarner Bros.
55th Annual Primetime Emmy Awards - Press Room
Jon Stewart and his team win the first of many Emmys for The Daily Show in 2003.Chris Weeks—FilmMagic/Getty Images
The 78th Annual Academy Awards - Jon Stewart Portraits
Jon Stewart hosts the 78th Academy Awards in 2006.Academy of Motion Picture Arts—WireImage/Getty Images
Stewart has a cameo as himself on The Simpsons in 2008 in the episode "E Pluribus Wiggum."Fox
Jon Stewart And Stephen Colbert Hold Rally On National Mall
Steven Colbert and Jon Stewart host the Rally To Restore Sanity And/Or Fear on the National Mall on Oct. 30, 2010 in Washington, DC. Win McNamee—Getty Images
US President Barack Obama (L) tapes an i
Jon Stewart interviews President Barack Obama on The Daily Show at the Harman Center for the Arts in Washington, DC, Oct. 26, 2010.Jim Watson—AFP/Getty Images
51st USO Armed Forces Gala & Gold Medal Dinner - Inside
Jon Stewart speaks at the 51st USO Armed Forces Gala & Gold Medal Dinner on Dec. 13, 2012 in New York City.Michael Loccisano—Getty Images
ROSEWATER, front, from left: Gael Garcia Bernal, Jon Stewart, on set, 2014. ©Open Road
Stewart makes his directorial debut in the 2014 drama Rosewater.Open Road Films
Jon Stewart announces his retirement for the end of 2015.Comedy Central

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Write to Tessa Berenson Rogers at tessa.Rogers@time.com