Jay Leno’s 20th Anniversary: 20 Memorable ‘Tonight Show’ Moments

ALT On May 25, Jay Leno celebrated his 20 year anniversary as the host of The Tonight Show. The episode’s guests included former Secretary of State Colin Powell and U.S. Army colonel and Battleship star, Gregory Gadson.

Leno might be one of the most consistent targets for mockery in the late night business, but his viewership has proven that he’s doing something right. You have to admit, the past 20 years have delivered some memorable moments to the Tonight Show audience, whether you’re more of a Team Coco person or not.

Below is a segment from Leno’s 20th Anniversary opening monologue, wherein he briefly touches upon his milestone and then goes on to crack jokes at the usual round of ridiculous current events. But stay tuned after the video for our 20 Memorable The Tonight Show with Jay Leno Moments.

20 Memorable The Tonight Show with Jay Leno Moments

May 25, 1992: First Tonight Show with Jay Leno broadcast, featuring Billy Crystal as Leno’s first guest.

May 20, 1993: Leno enjoyed a very intoxicating farewell to the NBC series Cheers with several members of the starring cast, including Ted Danson, Woody Harrelson and Kelsey Grammer. In keeping with the bar-theme of their sitcom, the live segment was filmed at the Boston tavern that provided the exterior shots for the program. Also in the spirit of the show’s alcohol-oriented nature, the entire cast was visibly drunk.

May 6, 1994: Comedian Bobcat Goldthwait set a chair on fire on The Tonight Show. As you do. 

March 2, 1995: A memorable parody of the O.J. Simpson trial: the Dancing Judge Lance Itos!

July 10, 1995: Hugh Grant owned up to his publicized reckless behavior — Grant had been arrested for lewd public conduct and for soliciting a prostitute — on the Tonight Show. Leno blatantly asked his guest, “What the hell were you thinking?” and earned his first ratings victory over The Late Show.

November 30, 1995: Howard Stern ran amok as a Tonight Show guest, with two porn stars in tow, provoking them to kiss on air. The radio host monopolized attention from the audience during the segment meant to focus on the episode’s other guests, film critics Gene Siskel and Roger Ebert. Leno reportedly walked off set (though the incident was edited out before broadcast).

March 13, 2000: Law & Order star Angie Harmon accepted a proposal from her boyfriend, professional football player Jason Sehorn, on the air. Adorable. 

June 21, 2001: In response to the California power outages, Leno hosted The Tonight Show Unplugged: an episode illuminated completely by candlelight and flashlights placed around the studio.

September 18, 2001: The first The Tonight Show broadcast following the World Trade Center attacks on September 11. Leno honored the New York City firefighters and police officers and Senator John McCain was the featured, patriotic guest.

May 12, 2003: Jay Leno switched places with Today Show host Katie Couric. Wackiness ensued.

August 6, 2003: Arnold Schwarzenegger announces his candidacy for governor of California on The Tonight Show and thus, the nation witnessed the birth of the Governator.

November 1, 2004: Bostonian Leno welcomed the Boston Red Sox to The Tonight Show following their first World Series victory since 1918. Wicked.

January 24, 2005: Following the death of The Tonight Show legend Johnny Carson, Leno paid tribute with a show dedicated to his predecessor. Carson’s sidekick Ed McMahon and regular guest Don Rickles gave Leno a hand.

March of 2005: In light of his legal prohibition from talking about the Michael Jackson trial (due to being a witness), Leno brought on a series of comedians to deliver jokes about the highly publicized situation. There is always a loophole!

April 8, 2005: Jay Leno vs. Hollywood icon Paul Newman in an unforgettable go-cart race. Although Newman defeated the Tonight Show host, Leno has referred to this as one of his favorite moments in the program’s history.

July 20, 2006: Colin Farrell was accosted by his “first stalker” on set during a Tonight Show interview. Somehow, Farrell’s stalker actually managed her way past security and onto the set, before being physically removed by Farrell himself, who could be he heard telling her that she was “insane.” 

Late 2007, Early 2008: Leno enjoyed a lot of press during the WGA Writer’s Strike, for behavior such as vocally supporting the strikes’ cause and for “burying the hatchet” with fellow talk show host Jimmy Kimmel (who has long been on the David Letterman side of the late night feud).

March 19, 2009: Barack Obama became the first sitting president to make an appearance on The Tonight Show. It was a good night for Leno, but quite a controversial one for the president, when he made a questionable joke, comparing his own athletic abilities to performances in the Special Olympics.

May 29, 2009: Jay Leno bade farewell to The Tonight Show… temporarily. Conan O’Brien, Leno’s successor, was the featured guest — a gesture that was warm-hearted at the time, but just seems ironic in light of Leno’s “reclaiming” of The Tonight Show in 2010.  

March 1, 2010: Welcome back, Jay Leno! Jamie Foxx and Olympic skier Lindsey Vonn served as his homecoming guests.


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