10 Memorable Moments From Jay Leno’s ‘Tonight Show,’ Now 30 Years Old

The Tonight Show With Jay Leno Hugh Grant
NBC/Courtesy: Everett Collection

From the time he started hosting The Tonight Show on May 25, 1992, to the time he handed the mic to Jimmy Fallon on February 6, 2014, Jay Leno hosted more than 4,600 episodes of the NBC late-night show, even more than predecessor Johnny Carson.

With the 30th anniversary of his Tonight Show debut upon us, we’re revisiting 10 memorable moments from the Leno era, everything from an on-air proposal to a stalker encounter to a go-kart face-off. Scroll down to see these headline-making moments.

Bobcat Goldthwait lights a chair on fire

In his 1994 appearance on the show, comedian Bobcat Goldthwait took a lighter to one of the guest chairs on the Tonight Show set. He was later given a fine of $3,888 after he pleaded no contest to a charge of recklessly causing a fire, according to the Los Angeles Times. (And as you can see here, the moment made it into an episode of The Larry Sanders Show, an HBO comedy about a fictional late-night show.)

Hugh Grant talks about lewd conduct bust

Hugh Grant’s 1995 Tonight Show appearance came soon after the actor was caught in a compromising position with a sex worker and arrested for lewd conduct. So, of course, Leno had to ask, “What the hell were you thinking?”

In his stammering response, Grant replied, “I think you know in life, pretty much, what’s a good thing to do and what’s a bad thing. I did a bad thing, and there you have it.”

Howard Stern makes a scene

Leno actually stormed off the Tonight Show set during a 1995 taping, after shock jock Howard Stern fondled and had his toes sucked by his two female companions on the show, as the Orlando Sentinel reported at the time. At the end of the episode, Leno asked critics Roger Ebert and Gene Siskel, the other guests booked for that show, to come back on a “normal night.”

Angie Harmon gets engaged

Law & Order and Rizzoli & Isles star Angie Harmon was shocked in 2000 when her beau at the time, New York Giants player Jason Sehorn, came out on set to propose to her, with fellow guest Elton John watching on. “Look at that ring.” Leno quipped, as Sehorn brandished a sparkler. “Even Elton is jealous.” The couple has since divorced.

Leno goes unplugged

For one episode in 2001, The Tonight Show put the (metaphorical) spotlight on California’s energy crisis, with Leno turning off the studio lights and hosting the chat-fest by the light of candles and flashlights.

Katie Couric takes over

In a ratings ploy, NBC had Katie Couric and Jay Leno switch places in 2003, with her hosting The Tonight Show and him co-anchoring Today. And it worked: Couric’s Tonight Show episode earned the late-night show its biggest audience in three years. “It was an outstanding stunt — and she charmed the audience,” former NBC entertainment chief Warren Littlefield told the New York Post at the time. “It’s easy to see just how broad her talent range is.”

Paul Newman races Leno in a go-kart

Not only was Paul Newman the Oscar-winning star of films like Cool Hand Luke, Butch Cassidy and the Sundance Kid, and The Sting, he was also a famed auto racing enthusiast. And Leno, who shares the need for speed, challenged the actor to a go-kart race around the studio in a 2005 episode.

Colin Farrell’s “first stalker” crashes the set

As Colin Farrell promoted his film Miami Vice on The Tonight Show in 2006, a female audience member confronted him on stage. The actor led the woman off stage, asked the camera crew to stop filming, and later told the audience that the woman was his “first stalker,” according to eyewitness accounts cited by People.

Barack Obama makes history (and controversy)

In 2009, Barack Obama made the first appearance by a sitting U.S. president on a late-night TV talk show when he joined Leno on The Tonight Show. The historic interview, however, generated a bit of controversy when the then-POTUS said his bad bowling score was “like the Special Olympics or something,” a joke for which he later apologized.

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George W. Bush paints a picture of Leno

Speaking of U.S. presidents, Obama’s Oval Office predecessor George W. Bush joined Leno on The Tonight Show in 2013 and even gave the host a portrait of Leno that he had painted. “I can’t make fun of him now!” Leno joked.