Jay Leno Says Former ‘Tonight Show’ Staffer Is Why He Stopped Telling Jokes About Transgender People

“Here’s the thing: you’re only as good as your last joke,” the comedian and late night host told Bill Maher during a recent ‘Club Random’ episode.

Jay Leno Vivien Killilea/Getty Images for SiriusXM

Jay Leno says the reaction from a member of his former Tonight Show staff to a joke he made about transgender people resulted in him apologizing and promising to never make transgender people the target of his jokes again.

The former TV host and comedian shared the story while appearing as a guest on the latest episode of Club Random with Bill Maher. The two had been discussing his tumultuous history entering and exiting late night hosting gigs — including controversies involving David Letterman, Jimmy Kimmel and Conan O’Brien — when Maher began to tell Leno that he’s “a victim of the terrible last viable prejudice in America: ageism.”

“You have this idea in your head that you have to go out to pasture,” the Real Time host continued. “As I talk to you now, you’re exactly the same guy who was there then, so I don’t think your brain is diminished.”

Leno responded by saying that how he sees himself and frames his roller coaster through late night was because he’s “a huge believer in low self-esteem.”

“I think it is the key to success because when you don’t think you’re the smartest person in the room, you shut up and you listen,” he said.

He elaborates that that helped keep him in check while hosting the show for more than two decades, with the former host turning to his own team to help ensure he stayed humble.

“When I got The Tonight Show, I hired the best producer I could, the best director, who I thought were the best writers. I gave them contracts on a yearly basis, not 13 weeks. I said, ‘Do the best you can.’ We had the same crew for 22 years. When they would tell me the show sucked, I would go, ‘Why’d it suck?’ And they’d tell me why it sucked.”

When Maher interjects to ask Leno whether he’s referring to letting someone on his staff like a gaffer “say that to you,” Leno confirms that he did listen to the thoughts of more than just the show’s higher-ranking creative team members.

“My theory was anybody can pull the cord and stop the train,” he says. “I remember one time we had a guy in the basement who I didn’t know. I had done at the time a transgender joke, and I heard this guy was really hurt about it. So I go down to see him and he explained the situation.”

Leno says he listened to that staffer and said “I apologize” after hearing how it was hurtful. He then made a promise about his jokes going forward, noting that “here’s the thing: you’re only as good as your last joke.”

“I said you’ll never hear another transgender joke from me again,” Leno recalled. “He was so taken by the fact that he could bring this show to a screeching halt because of his one complaint. [He] turned out to be the greatest lighting guy or sound guy, whatever he did, that we had.”

“To me,” he finished, “that’s worked for me.”

Leno previously apologized for making racist jokes targeting the Asian community throughout his career, including while guest judging on America’s Got Talent — comments that had been heavily criticized by the Asian community for years.

In a 2021 conversation with Media Action Network for Asian Americans (MANAA) leader Guy Aoki, Leno addressed his perpetuation of stereotypes about North Korea and Koreans, dismissing that this was “another example of cancel culture” and instead was “a legitimate wrong that was done on my part.”

“At the time, there was a prevailing attitude that some group is always complaining about something, so don’t worry about it,” the comedian said. “Whenever we received a complaint, there would be two sides to the discussion: either ‘We need to deal with this’ or ‘Screw ’em if they can’t take a joke.’ Too many times I sided with the latter even when in my heart I knew it was wrong.”