Jay Leno Called Judd Apatow to Tell Him His Jokes Stunk

Young Judd Apatow was fearless, at least when it came to approaching his comedy heroes. He started Comedy Club, a show on his 125-watt high school radio station, as an excuse to cold-call comedians for interviews. Who says yes to a convo with a high school kid? “I was basically tricking everybody into speaking to me,” Apatow confessed to Graham Bensinger, “and nobody ever asked. The landscape was very different — no one wanted to talk to comedians.” 

Apatow’s it-doesn’t-hurt-to-ask approach landed him interviews with up-and-coming comedians like Jerry Seinfeld, Steven Wright and Garry Shandling.

Another comic on Apatow’s list was pre-Tonight Show Jay Leno. “I interviewed him at this comedy club, Rascals Comedy Club in New Jersey,” he explained. “You know, he just was so nice. Some people would be incredibly gracious and talk to me for like an hour. Leno was like that.”

But meeting Leno as a teen didn’t help Apatow land a writing gig when he was older. “I tried to write jokes for Jay Leno, and I sent him a whole bunch of jokes, and they probably were terrible,” Apatow told Jimmy Fallon on The Tonight Show this week. “And then one day he called my house. I lived with my grandma at the time. My grandma answered the phone at midnight and she's like, ‘Jay Leno’s on the phone!’”

A call from famous comedian Jay Leno! That’s a great night until Apatow learned Leno was phoning “to tell me that my jokes weren’t any good.” But the phone call wasn’t a complete disappointment. “He was so nice about it that I got excited that I could talk to him.”

Leno called Apatow again after one of his movies came out. “He said, ‘You know, I really love the movie.’ He’s like, ‘I’ll tell you the truth. I’ll tell you when it’s good. I told you those jokes weren’t good when you were a kid. I’m an honest arbiter of your quality.’”

Fallon remembered his own early rejection at the hands of a late-night legend. He brought out a copy of a letter he received from David Letterman’s staff after sending in a VHS tape of his early stand-up attempts. “Dear Jimmy,” the letter began. “Thank you for letting us take a look at your set. Unfortunately, we’re going to pass for now. Thanks again for thinking of Late Show.” 

The kicker was the final line: “Enclosed, please find the videotape you sent us.”

“They actually sent me the tape back,” laughed Fallon.

Apatow understood The Late Show’s rationale: “We don’t want it stinking up our office.”

He also empathized with the pain of rejection. “I remember sending a videotape to every booker of every comedy club in America, and I put a letter with it,” he told Fallon. “If you want to book me, check yes, and if you don’t, check no.”

The clubs couldn’t even be bothered to check the no box. “Not one responded in America,” Apatow said. “Nobody.”