1 of 16 Chris Haston/NBC
Leno Makes His Debut (May 25, 1992)
Three days after Johnny Carson retired, Leno took over hosting duties at The Tonight Show. Though many people (including Carson himself) preferred David Letterman to be the new host, Leno — who had made several appearances on The Tonight Show as a guest host and stand-up comedian — was selected. Comedian Billy Crystal, Leno's first guest, came full circle and also appeared on Leno's final episode on Feb. 6, 2014.
2 of 16 Margaret Norton/NBCU Photo Bank/Getty Images
Bobcat Goldthwait Lights a Chair on Fire (May 6, 1994)
Allegedly upset about the cancellation of The Arsenio Hall Show, comedian Bobcat Goldthwait took out his frustrations by pouring lighter fluid on a chair and setting it on fire during an appearance in 1994. Though it wasn't the first time Goldthwait had caused a scene on a late-night show, to say Leno wasn't amused by the stunt would be an understatement. Goldthwait was subsequently charged with a misdemeanor, pled no contest, and was required to replace the chair, pay a fine, and film a series of fire safety PSAs that aired in the Los Angeles area.
3 of 16 Margaret Norton/NBCU Photo Bank/Getty Images
The Dancing Itos Debut (March 2, 1995)
For better or worse, Leno sure mined as much "comedy" as he could out of the O.J. Simpson trial. The host added to the media circus surrounding the double murder with the Dancing Itos, a group of dancers dressed like presiding Judge Lance Ito (seen here from a March 16, 1995 appearance). And let's not forget, dancing prosecutor Maria Clark! Hilarious, right?!
4 of 16 Margaret Nprton/NBC
Hugh Grant 'Fesses Up (July 10, 1995)
The interview had barely begun when Leno got right to the dirt. "What the hell were you thinking?" the host asked Grant of his recent arrest for lewd conduct and soliciting a prostitute. Yet somehow, Grant's earnest stammering won us over — and won Leno his first ratings victory over The Late Show, which he would maintain for most of the rest of his tenure. Perhaps not coincidentally, Leno's Tonight Show won its only Emmy Award for Outstanding Variety Series later that year.
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Howard Stern Hijacks the Show (Nov. 30, 1995)
Leno had a hard time keeping his cool when Stern hijacked the interview by bringing two porn stars onstage to create "The Tonight Show's first lesbian kiss." The host tried to regain control when he moved on to interviewing film critics Gene Siskel and Roger Ebert, but when Stern began toe-sucking the women, Leno had enough and walked off set (though his exit was edited out before broadcast).
6 of 16 Paul Drinkwater/NBC
Angie Harmon's Proposal (March 13, 2000)
What's better than getting proposed to on national TV? Having Elton John sitting right beside you! After Leno showed off the actress' Glamour cover, an issue about the dos and don'ts of dating, he segued into her relationship with former New York Giants cornerback Jason Sehorn. Remaining coy, Harmon said she doesn't talk about her personal life. "What if he wanted to come out?" Leno asked. Of course, Sehorn did — and dropped to one knee. But did he get permission from Harmon's dad? Yup, and her pops walked out on stage as well. The two married in 2001 and have three kids.
7 of 16 Paul Drinkwater/NBCU Photo Bank/Getty Images
The Tonight Show Goes Unplugged (June 21, 2001)
In response to the continuous rolling blackouts throughout California, Leno turned off the bright lights in his studio as well for
8 of 16 Paul Drinkwater/NBC/Getty Images
Leno Honors New York Following 9/11 (Sept. 18, 2001)
In his first post-9/11 show, Leno forewent his usual comedy shtick to pay tribute to the victims and honor the New York City firefighters and police officers. The car and motorcycle aficionado teamed with Harley-Davidson to auction off a commemorative FXDL Dyna Low Rider that had been signed by various celebrities — including John Travolta, Tom Cruise and Denzel Washington — to raise money for the victims of the attacks. The bike reportedly went for $360,000 on eBay.
9 of 16 Paul Drinkwater/NBCU Photo Bank/Getty Images
Leno Switches Places with Katie Couric (May 12, 2003)
In the 20-plus years that Leno has hosted The Tonight Show, he has only once allowed someone else behind his desk. In a sweeps stunt, Leno traded jobs with Today co-anchor Katie Couric. Couric had fun playing comedian, especially showing off her legs after she ordered staff to change the layout of Leno's desk with a power saw. Leno, meanwhile, looked comfortable playing the straight man during his interview with Colin Powell on Today, though he did challenge him to a car race.
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Arnold Schwarzenegger's Gubernatorial Announcement (Aug. 6, 2003)
The Terminator star changed the face of politics when he appeared on The Tonight Show to reveal his big plans to rid California of incumbent Gov. Gray Davis by leading the recall charge. But that wasn't all. The actor then boldly proclaimed, "I'm going to run for governor of the state of California." Not one to let his fame go to waste, Schwarzenegger also uttered, "Hasta la vista, baby," the first of his many famous movie lines that he'd recite in what would be one of the most showbiz-infused campaigns ever.
11 of 16 Paul Drinkwater/WireImage
Leno Dedicates Show to Johnny Carson (Jan. 24, 2005)
A day after Carson died, Leno opened the show with a heartfelt monologue thanking his mentor. "We trusted Johnny," Leno said. "We trusted him to make us laugh, to entertain us, to speak for us with what was a truly an American voice. Johnny hosted this show for 30 years. Think about that, these days some NBC shows don't last 30 days. ... Johnny never went out of style." The host then reminisced with Don Rickles, Bob Newhart and Ed McMahon about their memories of Carson. Later, Drew Carey came on to introduce a montage of stand-up comedians, including himself, who got their big break from Carson. The show wrapped up with one of Carson's favorite artists, k.d. lang, singing her song "Simple."
12 of 16 Margaret Norton/NBC/Getty Images
Leno's Stand-Up Stand-Ins (March 2005)
It's rough being a celebrity sometimes. When Michael Jackson was on trial for child molestation charges in 2005 and Leno was called as a witness, the host was prevented from making any Jackson-related jokes on air. Instead, Leno called on a few good friends, including Roseanne Barr, Brad Garrett and Dennis Miller, to perform jokes he had written about the trial. Leno's gag order was eventually lifted, at which point he devoted an entire monologue to just the trial.
13 of 16 Margaret Norton/NBC/Getty Images
Colin Farrell Gets Accosted By a Stalker (July 20, 2006)
Where's the security? Audience members thought it was a skit when Dessarae Bradford leapt out of the crowd and ran up to Farrell midway through his chat. Farrell led her off stage to security as she shouted, "I'll see you in court" at him. (She had already unsuccessfully sued him for $5,000 harassing phone calls and texts at this point). Farrell reportedly called her "insane," while Bradford left behind a little something for Leno: a copy of her self-published book, Colin Farrell: A Dark Twisted Puppy on his desk. Aw, you shouldn't have. No, really.
14 of 16 Paul Drinkwater/NBCU Photo Bank/Getty Images
Obama Visits The Tonight Show (March 19, 2009)
Leno landed a big coup when Obama became the first sitting president to appear on a late-night talk show, visiting the program just two months after being sworn into office. Since then, POTUS has dropped by other late-night programs to, say, Slow-Jam the News, but Leno remains his favorite late-night guy. He's visited four more times, most recently in August 2013.
15 of 16 Paul Drinkwater/NBC/Getty Images
Leno Signs Off, Part I (May 29, 2009)
Leno signed off with what would turn out to be the first of two goodbyes to make way for Conan O'Brien — a transition that was announced in 2004 that Leno has now said he was never on board with. Greeted with a huge standing ovation, Leno opened by thanking all the important people who made the show possible over the past 17 years: "Michael Jackson, Monica Lewinsky and Bill Clinton." He closed it by inviting on stage all the children who had been born to staffers who met while working on the show — which turned out to be 68!
16 of 16 Paul Drinkwater/NBC/Getty Images
Leno Returns to The Tonight Show (March 1, 2010)
Just nine months after leaving, Leno returned to the Tonight Show desk when Conan O'Brien opted to resign instead of shifting back his start time to accommodate The Jay Leno Show. "It's good to be home," Leno said in his monologue. "I'm Jay Leno, your host. At least, for a while." Leno carried on with his usual segments (though he did need a new desk) and did not mention Conan by name, though he did name-drop some other folk. "I've got to admit that I'm a little nervous," he said. "Not because it's my first night back. Because I know that Dave and Oprah are watching."