JAN. 11, 1999
Stewart hosts his first Daily Show episode, with guest Michael J. Fox. Correspondent Stephen Colbert reports on merchandise inspired by Bill Clinton’s ongoing impeachment trial.
JULY 17, 1999
Comedy Central announces that The Daily Show will helm the network’s “Indecision 2000” presidential-race coverage. The show’s commentary on the election wins a Peabody Award.
SEPT. 20, 2001
Stewart shows his earnest side, abandoning satire in his first show after 9/11. He memorably opens the program by asking viewers, “Are you O.K.? We pray that you are, and that your family is.”
NOV. 4, 2001
The Daily Show wins its first of 20 Emmys, for Outstanding Writing for a Variety or Music Program.
OCT. 15, 2004
Stewart drops by CNN’s Crossfire to promote America (The Book). He winds up excoriating hosts Tucker Carlson and Paul Begala for failing to provide useful public discourse. He implores them to “Stop hurting America.”
NOV. 7, 2005
Barack Obama first appears on the show via satellite, as a U.S. Senator from Illinois. He is a guest six more times, as a Senator, presidential candidate and President.
MARCH 12, 2009
Stewart interviews Mad Money host Jim Cramer about the financial crisis and accuses him of shoddy reporting. Cramer defends himself but says, “We all should have seen it more.”
OCT. 30, 2010
Stewart and Colbert host the Rally to Restore Sanity and/or Fear on the National Mall, with more than 200,000 in attendance.
FEB. 23, 2011
Stewart interviews Donald Rumsfeld about the Iraq War, beginning the conversation with two words: “Apology accepted.”
JUNE 10, 2013
John Oliver steps in as host of The Daily Show for the summer (32 episodes), as Stewart takes a 12-week break to direct his feature-film debut, Rosewater, about a journalist imprisoned in Iran.
FEB. 10, 2015
Stewart announces his forthcoming retirement: “In my heart I know it is time for someone else to have that opportunity.”
AUG. 6, 2015
Stewart hosts his final episode before passing the reins to South African comedian Trevor Noah, who is set to take over on Sept. 28.
This appears in the August 17, 2015 issue of TIME.