When Jay Leno recalls those rough early days in Boston comedy, he has to laugh

By Nick A. Zaino III Updated July 14, 2023, 6:00 a.m

Before any dreams of hosting “The Tonight Show,” or being a big shot in the Los Angeles stand-up scene, or playing theaters like the Chevalier, where he’ll appear Aug. 4, Jay Leno was just a kid in Andover who wanted to crack people up. He considers himself lucky that he found encouragement in his early days, starting in high school when his teacher, Mrs. Hawkes, let him give a talk instead of writing a term paper. Leno is dyslexic, and had trouble in school, but he figured he could talk for 20 minutes with no problem.

“That was the first time in my life I enjoyed doing homework,” he says, speaking by phone from Los Angeles. “I went home and I wrote out what I was going to say, and then memorized it. Just kids stories, things that happened around school, you know, that kind of stuff. And I got a few laughs.”

That same teacher suggested maybe Leno could pursue comedy as a job, something he hadn’t thought was a possibility. He was working at McDonald’s in Andover at the time, and his guidance counselor had gone as far as to call a meeting to suggest to Leno’s parents that maybe he would be happy staying in that line of work. But Leno was only further encouraged to do comedy professionally when he won a talent show for McDonald’s employees with a stand-up routine. A couple of years later, in 1969, he made his professional debut at the Nameless Coffeehouse in Harvard Square, working in a duo with future TV writer and producer Gene Braunstein, his Emerson College roommate.

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