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.
Jon Stewart takes the reins as anchor of The Daily Show in 1999.Comedy Central/EverettStewart gets a cameo as Kevin Gerrity in the 1999 Adam Sandler movie Big Daddy.ColumbiaJay Leno interviews Jon Stewart on The Tonight Show With Jay Leno in 2000.NBC/Getty ImagesStewart plays Marion Frank Stokes in the 2002 black comedy Death to SmoochyWarner Bros.Jon Stewart and his team win the first of many Emmys for The Daily Show in 2003.Chris Weeks—FilmMagic/Getty ImagesJon Stewart hosts the 78th Academy Awards in 2006.Academy of Motion Picture Arts—WireImage/Getty ImagesStewart has a cameo as himself on The Simpsons in 2008 in the episode "E Pluribus Wiggum."FoxSteven 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 ImagesJon 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 ImagesJon Stewart speaks at the 51st USO Armed Forces Gala & Gold Medal Dinner on Dec. 13, 2012 in New York City.Michael Loccisano—Getty ImagesStewart makes his directorial debut in the 2014 drama Rosewater.Open Road FilmsJon Stewart announces his retirement for the end of 2015.Comedy Central
