Jay Leno reflects on favorite ‘Tonight Show’ memories, Letterman rivalry en route to MGM National Harbor

Hear our full chat on my podcast “Beyond the Fame with Jason Fraley.”

WTOP's Jason Fraley previews Jay Leno at MGM National Harbor (Part 1)

He became a household name by hilariously hosting “The Tonight Show” for decades every night on NBC.

On Saturday, comedian Jay Leno brings his standup tour to MGM National Harbor in Oxon Hill, Maryland.

“I’m having a good time,” Leno told WTOP. “I just took politics out of my act. I’m just so sick of it. You get to the point where you mention one candidate’s name and [the audience goes] ‘booo, yay.’ You start, ‘Today, Biden or Trump said,’ they want to know the punchline before they laugh at it, ‘is it pro-my guy or against?’ I just took it out and, boy, it makes a big difference, ticket sales are up like 30%. People just want to hear comedy and have fun.”

Born two miles north of Manhattan in 1950, Leno grew up loving cars and comedy from a young age.

“Anything that rolled, exploded and made noise I enjoyed,” Leno said. “I got into [comedy] when I was about 19. Prior to that, all the comedians had been [old] guys that grew up during the Depression: ‘These kids today!’ … Then you had a whole class of [George] Carlin, Richard Pryor, Robert Klein, suddenly there were comedians who were just a couple years older than me but had the same sensibilities that I had. That’s when the comedy boom began.”

As a rising standup comic, Leno made his first guest appearance on “The Tonight Show with Johnny Carson” in 1977, then became the show’s regular substitute host in 1987 before officially taking over hosting duties in 1992.

“The power of television back in those days was much stronger,” Leno said. “At night, Carson was the only thing on. … Johnny ruled the roost, so when you were on Carson, literally almost everyone in America saw you. The next day people would stop you on the street. Now you have to do a dozen TV appearances for people to go, ‘Who’s that?'”

During the 1990s late-night TV battle, roughly half of the audience watched Leno on NBC, while the other half watched David Letterman on CBS. The press was quick to paint it as a heated rivalry, considering Leno got the “Tonight Show” gig after it had looked like Letterman was being positioned as Carson’s heir apparent.

“It was a friendly rivalry, everyone else made it much worse than it really was,” Leno said. “David and I had a mutual admiration and still do. I think David admired me because I was loud and loquacious. I admired Dave because he was a great wordsmith, a great writer. … I was lucky enough to get the ratings, Dave was lucky enough to get the critics. … I think it helped, I think it made each show better, competition only improves the breed.”

Leno’s charm shined most when interacting with people on the street in his hilarious “Jaywalking” bits.

“That was my favorite thing,” Leno said. “We never spoke to more than 20 people a night because we had a show to do the next day and we always got something from everybody. My favorite question was: ‘How was Mount Rushmore formed?’ The answer we got more than once was ‘erosion.’ Not only did the wind and rain pick four presidents, it picked four of our greatest presidents! Just wind and rain and, ‘oh my God, it’s Thomas Jefferson!'”

In studio, he famously read actual newspaper typos in the beloved recurring segment “Headlines.”

“My favorite one was I said to the audience, ‘There’s a reason women make great advice columnists: Ann Landers, Dear Abby,’ but there was one called ‘Dear John.’ I read one: ‘I’m 31, my husband is 34, I got up to go to work, I got two miles from our home and the car stalled, I walked two miles back and when I walked in, I found my husband in bed with our 19-year-old neighbor. … What should I do?’ ‘Dear Heartbroken, a car can stall for many reasons.'”

His favorite celebrity guests included actor Sean Connery and former President Barack Obama. If the guest was fresh off a scandal, like Hugh Grant’s 1995 arrest, Leno gave them a backstage heads up of pending questions.

“It’s not an ambush show, I never liked those kind of things where you go, ‘How do you explain this Mr. So and So?'” Leno said. “I did say to him, ‘Look, I got to ask you, you can answer any way you want, but we can’t avoid it.’ I find that’s best. Sometimes you can win the battle but lose the war. A lot of times I would watch shows where a guest would just get humiliated by the host and the audience would laugh, but the guest would never come back.”

After hosting “The Tonight Show” from 1992 to 2009, Leno moved to a different time slot and relinquished the reins to Conan O’Brien, whose ratings dip caused NBC to panic and reinstate Leno from 2010 to 2014. We didn’t ask him about that whole controversy again this time because he previously addressed it on WTOP in 2017.

“Conan’s excellent,” Leno said. “What happened was basically just business. It really comes down to who you’re gonna make more money with. When they decided to switch off, my contract said I had five years left. Then, over the course of that five years, Craig Ferguson went opposite of Conan on CBS, his thing was climbing, and NBC was like, ‘Hmm, are we making the right deal here?’ … It’s too bad. I think I lost a friend at the time and so did he.”

The same year that his “Tonight Show” run ended, Leno visited D.C. to receive the 2014 Mark Twain Prize for American Humor at the Kennedy Center, which just named Kevin Hart next year’s recipient.

“It was great fun,” Leno recalled of the honor. “Let’s be honest, people usually campaign for awards like Emmys. You put yourself up for it. Or even the Golden Globes, you buy a lovely gift for a member of the Foreign Press, [but] this is one of those things where they just call you up one day. You don’t really apply for it, or ask for it, or ask to even be considered for it, so that’s why it was really cool.”

Most recently, he hosted “Jay Leno’s Garage” on CNBC from 2014-2022, followed by “You Bet Your Life” (2021-present), a Fox revival of the old NBC game show that was originally hosted by the legendary Groucho Marx.

“Someone said to me, ‘How did it feel replacing Groucho?’ I go, ‘The show ended in ’61, if you still remember Groucho, you’ve got to be over 90 years old,” Leno said. “I noticed the change for me when I would go, ‘My next guest has sold more albums than Elvis and The Beatles combined. Please welcome … who is this?!'”

WTOP's Jason Fraley previews Jay Leno at MGM National Harbor (Part 2)

Listen to the full conversation on the podcast below:

Jason Fraley

Hailed by The Washington Post for “his savantlike ability to name every Best Picture winner in history," Jason Fraley began at WTOP as Morning Drive Writer in 2008, film critic in 2011 and Entertainment Editor in 2014, providing daily arts coverage on-air and online.

Federal News Network Logo
Log in to your WTOP account for notifications and alerts customized for you.

Sign up