--- description: Take a look back at a 16-year-reign title: Watch Jon Stewart's 5 Greatest 'Daily Show' Moments image: https://static.time.com/v3/assets/bltea6093859af6183b/blt0c0ed6f9a5946e21/69876399a988ca32ba6aa1f3/458012744.jpg?branch=production&width=3840&quality=75&auto=webp&crop=16:9 ---  * [Entertainment](/section/entertainment/) ## Entertainment Update your preferences in [Account Settings](/account/preferences/) Close # Watch Jon Stewart's 5 Greatest _Daily Show_ Moments  by [Tessa Berenson](/author/tessa-berenson/)  ## Tessa Berenson Update your preferences in [Account Settings](/account/preferences/) Close Updated: Jan 17, 2024 5:05 PM CUTPublished: Feb 11, 2015 1:01 AM CUT  Host Jon Stewart at "The Daily Show with Jon Stewart" covers the Midterm elections with "Democalypse 2014: South By South Mess" on Oct. 28, 2014 in Austin, Texas. Host Jon Stewart at "The Daily Show with Jon Stewart" covers the Midterm elections with "Democalypse 2014: South By South Mess" on Oct. 28, 2014 in Austin, Texas.Rick Kern—Getty Images  by [Tessa Berenson](/author/tessa-berenson/)  ## Tessa Berenson Update your preferences in [Account Settings](/account/preferences/) Close Updated: Jan 17, 2024 5:05 PM CUTPublished: Feb 11, 2015 1:01 AM CUT There are many notable moments from [Jon Stewart’s 16 year reign at the helm of ](http://time.com/3704244/jon-stewart-the-daily-show-leaving/ "undefined")[_The Daily Show_](http://time.com/3704244/jon-stewart-the-daily-show-leaving/ "undefined")_,_ 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** _Read next:_ [_7 Potential Replacements for Jon Stewart on_ ](http://time.com/3704465/jon-stewart-the-daily-show-retiring-replacement-hosts/?xid=time%5Freadnext "undefined")[The Daily Show](http://time.com/3704465/jon-stewart-the-daily-show-retiring-replacement-hosts/?xid=time%5Freadnext "undefined") [_Listen to the most important stories of the day._](http://time.com/newsletter/the-brief/?sl%5Fautoplay=true&xid=spl-fullbrief-article "undefined") ### 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. 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