In January 1999, fresh-faced Jon Stewart took over The Daily Show desk. Over the past 16 years, he helped make Comedy Central a force in late-night, he redefined news coverage, earned 18 Emmys and was pronounced “America’s Most Trusted Newsman.” Stewart skewered politicians and the media, with the 24-hour news networks among his favorite targets. Young viewers tuned in night after night for the jokes (and for the news of the day) but it was those rare poignant moments, with Stewart reacting to 9/11, to the Eric Garner Grand Jury decision, that defined his tenure as much as the zingers. As an older and wiser Stewart prepares to leave his long-time TV home, here are some of his most memorable moments:

Indecision 2000 – Victory: Bush
December 13, 2000

9/11
September 11, 2001

Crossfire
October 15, 2004

Larry Craig
September 10, 2007

Jim Cramer
March 12, 2009

Glenn Beck
March 18, 2010

BP Oil Spill
May 3, 2010

Bill O’Reilly
September 27, 2010

Rally to Restore Sanity
October 30, 2010

Guantanamo Baywatch
June 12, 2012

The Eric Garner Grand Jury Decision
December 3, 2014