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.
“You had people with no money being entertained by people with no talent,” he said of those first gigs. “It was college students. Nobody could afford to go anywhere. So you just sort of entertain yourself.”
The first full-time comedy clubs wouldn’t start to open in Boston until the end of the 1970s long after he left town, so Leno took whatever he could get: college rooms where no one knew there was going to be entertainment, the short-lived Playboy Club and Hillbilly Ranch in Park Square. In a story he has often recounted, Leno played the Beachcomber in Revere and had to dodge lit cigarette butts flicked at him from the crowd, one of which landed on his shoulder and burned a good suit.
“Well, you have to understand, [that was] no different than any other gig that I played because they were all horrible,” he says. “See, the good thing about that was you never found out how terrible you were because nobody ever really gave you a chance. You know, people are throwing stuff at you and you’re opening for strippers and guys who are yelling. You don’t really know if it’s good or not. You know, I got through it. It was like the old joke, ‘What, and quit show business?’ ”
The gauntlet of rowdy club audiences likely weeded out a lot of hopefuls, but not Leno. “I never got discouraged because I had real jobs, and real jobs really suck,” he says. “At least comedy, you know, it’s only a bad job for 20 minutes or a half-hour. It’s not a bad job for eight hours.”
Right now, Leno can’t do anything but stand-up comedy. CNBC switched up formats and dropped “Jay Leno’s Garage.” Leno reports he is close to a deal to bring the show back elsewhere, likely in the summer of 2024. Because of the writers’ strike, he says a hosting gig for a “You Bet Your Life” reboot is on hold until next year. But if stand-up is his only job at the moment, “that’s fine with me,” he says.
Leno estimates he plays a minimum of 150 dates a year. He gets around the country to do theaters like the Chevalier, but closer to home in Los Angeles, he appears regularly at Flappers Comedy Club in Burbank and maintains a long-standing gig at the Comedy & Magic Club in Hermosa Beach. “I’ve been in the Comedy & Magic Club every Sunday since ‘78,” he says. “[Jimmy] Carter was president when I started.”
He enjoys coming back to his old stomping grounds when he can. There is something inherently funny to him about the brusqueness of New England. “It’s just you have that New England work ethic,” he says, “when you grow up on a diet of ‘Ethan Frome’ and ‘Silas Marner.’ And life is awful, and then you die. And then it gets worse.” One thing in particular that tickles Leno is receiving what he calls a “New England Compliment.” Someone here will say something like, “I don’t care for you personally, but my wife’s a big fan,” he says. “Brutally honest, which really makes me laugh.”
The comedy business looks a lot different 50-plus years removed from Leno’s first gigs. Boston has many more venues for comedy, the late-night TV scene has expanded since Leno was hosting, and people are watching stand-up on their phones. But Leno believes good comedy is timeless. Buster Keaton and Charlie Chaplin are still funny. Same with George Carlin and Robert Klein. “A funny line lasts forever,” he says. “Mark Twain is always funny. It doesn’t matter what era he lives in, it’s still relatable.”
Leno says he still loves stand-up comedy as much as he did when he was dodging lit cigarettes or trying to get the attention of bored college students. “I just thought it was the greatest thing in the world,” he says. “I thought, ‘I’m gonna do this until I absolutely have to get a job.’ And luckily, I didn’t have to get a job.”
At the Chevalier Theatre, 30 Forest St., Medford. Aug. 4 at 7:30 p.m. $55-$120. www.chevaliertheatre.com
Nick A. Zaino III can be reached at email@example.com.