The Best And Worst Guests On The Tonight Show With Jay Leno

The Tonight Show has featured numerous hosts over the years, including Johnny Carson, Jack Paar, and Jimmy Fallon, and one of the most memorable was Jay Leno. He hosted the late-night talk show from May 25, 1992, to February 6, 2014, and interviewed thousands of popular guests from the entertainment industry.

Leno was constantly outdoing his competitors, such as David Letterman and Conan O’Brien, in ratings wit his witty jokes and outlandish guests. Leno certainly had favorite celebrities on the show, but also had a few who he couldn’t stand. Keep reading to reminisce about the most iconic guests from The Tonight Show with Jay Leno.

Bobcat Goldthwait Set His Chair On Fire

bobcat goldthwait and jay leno next a chair caught on fire
NBCUniversal Television Distribution
NBCUniversal Television Distribution

Jay Leno’s interview with comedian Bobcat Goldthwait took place on May 9, 1994, and came with a completely unexpected outcome. The comic purposely set his guest chair on fire in protest of the cancellation of The Arsenio Hall Show.

Goldthwait was later fined over $3,000 to cover the cost of the damage to the chair and was required to make several public service announcements about fire safety. Fans of the show thought Goldthwait had been banished from appearing on The Tonight Show, but Leno brought him back a week later.

Colin Farrell’s Stalker Interrupted His Interview

colin farrell and jay leno conversing
Kevin Winter/Getty Images
Kevin Winter/Getty Images

In the July 20, 2006, episode of The Tonight Show with Jay Leno, Colin Farrell was there as the primary guest. During his interview, his stalker, named Dessarae Bradford, got through security and walked onstage as the cameras were rolling. The audience was completely flabbergasted as they watched her throw a book on Leno’s desk.

Farrell escorted her off the stage as she shouted, “I’ll see you in court,” to which he responded, “Darling, you’re insane!” He handed her over to the Burbank police and later requested a restraining order.

Angie Harmon Says “Yes” Live On Air

Jason Sehorn proposing to Angie Harmon on Jay Leno
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NBC/Getty Images

Nothing draws ratings as much as a surprise proposal. On the March 13, 2000, episode of the show, Leno was interviewing Elton John and Law & Order star Angie Harmon. Leno started asking Harmon about her boyfriend Jason Sehorn of the New York Giants, but she tried to dodge his questions.

Out of nowhere, Sehorn appeared carrying a diamond ring and went down on one knee. He asked Harmon to marry him and she accepted. Later in the broadcast, Leno brought out her father to give permission to the marriage.

Paul Newman Puts The Pedal To The Medal

paul newman and jay leno driving go-carts
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NBC/Getty Images

Most knew Paul Newman as one of the most iconic actors in cinematic history, but he also loved racing. In The Tonight Show episode dated April 8, 2005, he and Leno did a hilarious go-cart race around the soundstage. It wasn’t even a close call, with Newman taking the lead and winning the race.

They decided to do the race because Newman didn’t enjoy just sitting and chatting and was able to show off his racing talent on TV. After Newman’s passing, he gave some of his race cars to Leno, who loves to take them out on drives.

Jimmy Kimmel Almost Reconciled With Jay Leno

jimmy kimmel and jay leno posing for a photo
NBCUniversal Television Distribution
NBCUniversal Television Distribution

Television was without writers during the Writer’s Guild Association strike, which meant that all late-night hosts were forced to write their shows completely on their own. The January 10, 2008 episode had two former rivals, Jimmy Kimmel and Jay Leno, hosting the show together.

They were feuding beforehand because Kimmel, a longtime David Letterman fan, thought he should’ve been chosen to host The Tonight Show. They finally were able to reconcile on air, but it didn’t last. Five years later Kimmel bashed Leno saying he “hasn’t been good at stand-up in 20 years.”

Arnold Schwarzenegger Made A Career Change On The Tonight Show

arnold schwarzenegger with jay leno
Kevin Winter/Getty Images
Kevin Winter/Getty Images

It was quite a momentous occasion when Arnold Schwarzenegger appeared on The Tonight Show with Jay Leno on August 6, 2003. He took the opportunity to make the huge announcement that he would be running in the upcoming recall California governor race.

Many think the promotion on the late-night show helped boost his credibility and popularity and he ended up winning just two months later. Schwarzenegger would go on to appear on the show several more times and Leno spoke on behalf of him at some of his campaign rallies.

Leno Was Visibly Angered By Howard Stern’s Appearance

howard stern and jay leno
NBCUniversal Television Distribution
NBCUniversal Television Distribution

It was a rare thing to see Leno get visibly upset with a guest, but he couldn’t hide his anger during the November 30, 1995, taping of his show. The guest was Howard Stern. He brought along a couple of women and continued to act inappropriately with them in front of the audience, even though Leno asked him to stop.

The crowd went wild when Stern disobeyed him. Leno got so furious that he left the show early by walking off when they were still on the air. Most of what they filmed was edited out of the show.

Conan O’Brien And Jay Leno’s Massive Conflict With NBC

conan o'brien and jay leno
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Kevin Winter/Getty Images

Two of NBC’s biggest ratings leaders were Jay Leno on The Tonight Show and Conan O’Brien on Late Night. When O’Brien’s contract was ending, NBC told him he could take over for Leno, but didn’t let Leno know until he had signed his contract extension with the network.

May 29, 2009, was supposed to be Leno’s last show, so he had O’Brien on to introduce him to his audience. After the transition, the ratings started to slip. Leno’s new show got an early time slot while they pushed O’Brien back to a later one. O’Brien was furious and left the show eight months later, with Leno returning in his place.

Leno Confronts Kanye West Over Taylor Swift Dispute

kanye west and jay leno
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NBCUniversal Television Distribution

One of the most infamous pop culture moments of the 2000s was when Kanye West interrupted Taylor Swift’s acceptance speech at the 2009 MTV Video Music Awards. West wasn’t in his right mind and took the microphone from Swift, saying that Beyoncé should have won.

The night after the incident, West appeared on the September 14, 2009, episode of The Tonight Show. There was no way to avoid what he’d just done, so Leno confronted him about it. West was remorseful and wanted to apologize to Swift. Leno even brought up his late mother, asking West, “What would she think?” West broke down in tears.

Heidi Klum’s $11 Million Wardrobe Malfunction

heidi klum, martin short, and jay leno holding up suit jackets
Kevin Winter/Getty Images
Kevin Winter/Getty Images

Heidi Klum was put in an embarrassing situation when she appeared on the October 14, 2003, episode of The Tonight Show alongside Martin Short. Klum was wearing diamond-studded undergarments worth a total of $11 million and one of them came undone while she was live on the air.

When she noticed there was something wrong she froze and tried to hold onto her shirt. In order to fix her wardrobe malfunction, Leno and Short took off their suit jackets and held them up over her, so she could readjust the straps.

Hugh Grant Heavily Bumped Leno’s Ratings

hugh grant and jay leno
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NBC/Getty Images

Up until July 10, 1995, Jay Leno’s ratings never surpassed those of David Letterman. That all changed when he had Hugh Grant on the show. Grant had recently been arrested for lewd conduct and was a top tabloid target. The public tuned in to hear his side of the story.

Leno got straight to the point and asked him what happened. Grant responded, “I think you know in life what’s a good thing to do and what’s a bad thing, and I did a bad thing…and there you have it.” This was the first time Leno beat Letterman in the ratings and he continued to do so in every episode thereafter.

Who Could Forget The Dancing Itos?

the dancing itos performing a dance
NBCUniversal Television Distribution
NBCUniversal Television Distribution

The 1990s were full of memorable moments in history and one that gained massive media attention was the O.J. Simpson trial. Leno thought making fun of the trial on his show would be hilarious, so he brought on a dance group called The Dancing Itos on March 2, 1995.

They got the name because they were dressed up as Judge Lance Ito and even brought in a Marcia Clark lookalike for a show later in the month (pictured). The Dancing Itos eventually became an on-going gag with recurring musical numbers that reflected what was currently happening with the trial.

The Tonight Show With Katie Couric

katie couric hosting the tonight show
Kevin Winter/Getty Images
Kevin Winter/Getty Images

On May 12, 2003, Leno decided to switch things up about by trading jobs with Katie Couric. He went in her place on The Today Show, while Couric came over and guest-hosted The Tonight Show. It was designed as a publicity stunt for both of the shows.

Couric ended up interviewing Mike Myers and Simon Cowell, while Leno spent time talking to Rudy Giuliani. Although it was rare to have someone else host a talk show at the time, it is now quite common for TV hosts like Jimmy Kimmel and Ellen DeGeneres to have other celebrities fill in for them.

Leno Admits Who Was Hardest To Interview

buzz aldrin and jay leno wearing trenchcoats
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NBC/Getty Images

Having a talk show can be a lot of fun, but there are times where it can be really frustrating. Something that really got on Leno’s nerves was when his guests wouldn’t have a lot to say during the interviews. Robert De Niro often gave him one-word yes or no responses.

This also happened when he interviewed Buzz Aldrin on August 21, 1996. Leno asked Aldrin, “What’s it like to walk on the moon, Buzz?” Aldrin simply replied, “Cool.” He tried to get Aldrin to elaborate, but he didn’t respond.

Roger Moore’s Accent Threw Leno Off

roger moore and jay leno
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NBC/Getty Images

Even a few decades after his interview with Roger Moore, Leno still remembers how problematic it got. Moore appeared on the March 30, 1990, episode of The Tonight Show and the two started talking about their houses in Los Angeles and Palm Springs.

Moore added that he and his wife enjoy going to Indio, which is a town near Palm Springs. His accent made Leno think he said India and he joked with him, asking how he goes there every weekend. Moore got annoyed that Leno couldn’t understand what he was saying, but he eventually figured it out after the interview was over.

Here’s Johnny

ed mcmahon and jay leno
Paul Drinkwater/WireImage/Getty Images
Paul Drinkwater/WireImage/Getty Images

When most think of The Tonight Show, they usually remember the episodes hosted by Johnny Carson. Leno frequently performed stand-up during the Carson days and was very personable, so he was chosen as Carson’s successor. January 24, 2005, the day after Carson passed, Leno did a tribute show for him.

He reminisced with guests Ed McMahon, Bob Newhart, and Don Rickles. Later, Drew Carey came on the show to introduce a group of stand-up comedians who got their start on The Tonight Show with Johnny Carson. Carson’s favorite musician, k.d. lang, closed out the show.

How Leno Dealt With An American Tragedy

Stephen Stills, Graham Nash, and David Crosby with Jay Leno
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NBC/Getty Images

Following the events that took place on September 11, most TV programs temporarily went off the air. When his show returned on September 18, 2001, Leno paid tribute to America by opening with a shot of the American flag and honoring the firefighters, police, and rescue workers who lost their lives.

He had Crosby, Stills & Nash on to perform “My Country, ‘Tis of Thee.” He also organized the auction of a Harley-Davidson motorcycle signed by celebrities, where the proceeds would go to 9/11 organizations. In the numerous episodes that followed, Leno left in the clip of the large American flag waving during his opening monologue.

Homer Simpson Shook Things Up

homer simpson and a
NBCUniversal Television Distribution
NBCUniversal Television Distribution

On July 24, 2007, The Tonight Show went animated when Homer Simpson of The Simpsons delivered the opening monologue. After about a minute of failing jokes about NBC, GE, and Rosie O’Donnell, a “Simpsonized” Leno came out to get Homer to leave the stage.

Homer ended the bit by being upset that the fruit basket had fruit, instead of cookies. The main reason Homer temporarily left Fox to visit The Tonight Show on NBC was for a publicity stunt to promote The Simpsons Movie, which was coming out in a few days.

A Farewell To Cheers

cast of cheers with jay leno
NBCUniversal Television Distribution
NBCUniversal Television Distribution

Cheers was one of the most successful sitcoms of all time, lasting 11 seasons and 275 episodes. Its finale aired on May 20, 1993, so Leno decided to take his show on the road to Boston to celebrate this massive achievement.

He got to interview most of the cast including Ted Danson, Rhea Perlman, John Ratzenberger, and Kelsey Grammer. Since the cast was thrilled that they had reached this milestone, they were not in their right minds after being influenced by some liquid courage. Some cast members didn’t even realize they were live on television.

Billy Crystal Was There For The Whole Journey

billy crystal and jay leno
Kevin Winter/Getty Images
Kevin Winter/Getty Images

One of The Tonight Show’s most frequent guests was actor and comedian Billy Crystal. He had the honor of appearing in the first episode dated May 25, 1992 and the final episode on February 6, 2014. In his first appearance, he made a joke about Johnny Carson leaving, with a spoof of Bette Midler’s “You Made Me Love You.”

In the final episode, Crystal surprised Leno by performing another musical spoof, this time to the tune of “So Long, Farewell” from The Sound of Music. He was joined by special guests Jack Black, Kim Kardashian, Oprah Winfrey, Carol Burnett, Jim Parsons, Sheryl Crow, and Chris Paul.