Updated: August 4, 2015 2:58 PM [ET] | Originally published: February 10, 2015 8:01 PM EST ;
T here 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
VIDEO
Stewart schools Glenn Beck
Indecision 2000
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See Jon Stewart's Career Over the Years 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 Jay Leno interviews Jon Stewart on The Tonight Show With Jay Leno in 2000. NBC/Getty Images Stewart plays Marion Frank Stokes in the 2002 black comedy Death to Smoochy Warner Bros. Jon Stewart and his team win the first of many Emmys for The Daily Show in 2003. Chris Weeks—FilmMagic/Getty Images 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 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 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 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 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 More Must-Reads from TIME Donald Trump Is TIME's 2024 Person of the Year Why We Chose Trump as Person of the Year Is Intermittent Fasting Good or Bad for You? The 100 Must-Read Books of 2024 The 20 Best Christmas TV Episodes Column: If Optimism Feels Ridiculous Now, Try Hope The Future of Climate Action Is Trade Policy Merle Bombardieri Is Helping People Make the Baby Decision