‘What The Hell Were You Thinking?’: Jay Leno’s Most Memorable Interviews

Whether you love him or hate him, two-time host of The Tonight Show Jay Leno deserves the respect that comes with having been a fixture on late night comedy television for more than two decades, and a ratings champion for the bulk of that time. He has wrestled Hulk Hogan, donated incredibly expensive cars to wounded veterans, and done many other good things throughout his career. He’s done other stuff, too, but this isn’t about that. Instead, we’re going to look back at the chin’s career and re-visit 13 of his most memorable interview moments for his 65th birthday.

Hugh Grant talking about his prostitution arrest? Check. The Governator announcing his candidacy? Definitely. Bobcat Goldthwait setting his chair on fire? You betcha.

The Governator

Incumbent California Governor Gray Davis wasn’t having such a good time in 2003. The state’s ongoing electricity shortages and escalating utility rates forced a gubernatorial recall, forcing a new election. Arnold Schwarzenegger officially announced his bid for the seat on The Tonight Show and won.

Hugh Grant Did A No-No

In 1995, Hugh Grant was arrested after he was caught with Hollywood prostitute Divine Brown. His film Nine Months was just about to come out, and he’d been scheduled for numerous press interviews. He opened up to Leno about the incident when the host bluntly asked him, “What the hell were you thinking?”

Jimmy Kimmel Hijacks Leno’s Segment

Throughout the 2009 “Tonight Show Wars” many media personalities and celebrities piped in on occasion — riffing at the expense of NBC, Leno, and Conan O’Brien. Jimmy Kimmel was one of Leno’s most vocal antagonists, so when the latter invited him onto The Jay Leno Show for a segment, Kimmel used the opportunity to bury the knife.

Coming to America

Of all the wonderfully inane things Donald Trump has done over the years, perhaps his most entertaining was his one-man crusade against President Obama’s supposed lack of a U.S. birth certificate. When the President appeared on The Tonight Show in 2012, Leno’s writers decided to make light of the situation.

Presidential Painting

Former President George W. Bush famously took up painting after leaving the Oval Office. He’s no Picasso, but he can at least paint a recognizable-enough portrait of Leno. Bush brought the painting during his 2013 visit on The Tonight Show.

Kanye West Apologizes To Taylor Swift

Unless you don’t use the Internet (which you totally do since you’re reading this, liar), you’ve probably heard about a little incident involving Kanye West, Taylor Swift, and Beyonce at the 2009 MTV Video Music Awards. The response to Kanye’s outburst was swift, especially online. But he still had the balls to appear on The Jay Leno Show the following week and apologize for his behavior.

Paul Newman Plus Go-Karts Equals Fun

If Paul Newman tells you to “pray for your life” before racing him on a go-kart track, you’d better do it. The late actor beat Leno by a long shot during a segment from his 2005 Tonight Show interview.

He Definitely Started The Fire

In 1994, Bobcat Goldthwait doused his chair in lighter fluid and set it on fire. He was apparently mad about Paramount’s decision not to renew The Arsenio Hall Show or something. (“Arsenio” sounds like “arson,” no? Makes. You. Think.) The incident became the basis for an episode of The Larry Sanders Show.

Leno’s Love Connection

Leno tried his hand at being a love guru when he helped Jason Sehorn of the New York Giants propose to actress and fashion model Angie Harmon. Not only that, but Leno also brought on Harmon’s father to “approve” Sehorn’s proposal. I’m not sure if Elton John was also there to approve, or if it was just a happy coincidence.

Howard Stern’s First Appearance

The radio shock jock came onto the program in 1992, back when America was still learning his name. His radio show was becoming incredibly popular, and it seemed like it was getting to his head when he decided to commandeer Leno’s show.

That Time Stern Came With Two Porn Stars

Three years later, Stern returned to The Tonight Show with two scantily clad models to promote his new book. Why? Because, Stern said, Leno needed a “ratings boost.” With that in mind, Stern encouraged the models to break new ground by performing the program’s first lesbian kiss.

Leno and Stern don’t exactly get along nowadays.

Robin Williams In Las Vegas

Anytime Robin Williams went on the program, you knew it was going to be a good one. There are countless videos of the late comedian doing his thing on Leno’s show (and other late night shows). But perhaps one of the most memorable was his 1995 visit to The Tonight Show‘s week in Las Vegas. Censors had to cut away from Williams several times because, as always, many of his improvised bits included, erm, “gestures.”

Power Outage? What Power Outage?

So, obviously having Williams on is a blast, but what about when he’s there with a friend? He and Billy Crystal famously came onto the program in 1997 when much of California was suffering from rolling blackouts. The studio lost power briefly, but that didn’t stop the pair from entertaining Leno and the audience.