Jay Leno: Life is Funny

Andrew Szanton
10 min readMar 8, 2022

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JAY LENO, the comedian and former host of “The Tonight Show,” has had a long career, and is a nice person, by show business standards. For instance, when someone asks permission to use an old clip of his from “The Tonight Show,” Leno always says yes — unless it’s for porn. And even then he doesn’t say, “You’re a creep.” He says: ‘I’m sorry.’

Jay Leno

Yet two of his comedy host peers, David Letterman and Conan O’Brien, have been intensely annoyed with Leno. For a nice and amusing man, Leno has sharp elbows.

As a child in Andover, Massachusetts, Jay had dyslexia that was never diagnosed. He had a lot of trouble reading, and was never a great student — but he learned to maximize the things he could do. He never missed class. He listened to everything and soaked things up and worked on his memory. He told himself: ‘You’re not that bright; you have to WORK HARD.’

And he saw the humor in life, and people enjoyed being around him. He felt he had a decision to make about whether life was hard or life was funny, and he decided life was funny.

At age 7, Leno saw Elvis Presley in the movie “Loving You.” Elvis sang “Teddy Bear” and the girls went crazy. Jay decided to take guitar lessons, and become a rock star. The only problem was he had no talent for rock and roll. And he realized he didn’t even really like music. He didn’t like sports much, either.

But cars… Now, there was something fascinating.

In 4th grade, the teacher was telling Jay’s class how mean and cruel the Sheriff of Nottingham was. She asked the class why the sheriff had boiled Friar Tuck in oil? Jay said “Because he was a fryer.” A few kids laughed, and Jay was hooked. He wanted to tell more jokes and hear laughter again.

Jay’s mother, Catherine, came to the United States from Scotland at the age of 11. Her family had the stereotypical Scots values: very reserved, very frugal. Jay would go over to his Scottish aunt’s house, and she’d serve stale scones and warm Coca-Cola. When Jay asked her why she didn’t refrigerate the Coke, she said she wasn’t going to pay good money to refrigerate something she hadn’t even drunk yet.

One of Catherine Leno’s favorite sayings was: “There’s a time to be funny and a time to be serious.” But Jay realized at an early age that, to his mother, there was never a time to be funny. Humor was dangerous because it was subversive. She believed in order and rules. Jay would be silly and, like clockwork, she would say “Jay, there’s a time to be funny and a time to be serious.”

Once the family took a trip to Disneyland, and Jay was cracking jokes.

“Not here,” his mother said solemnly.

“Then WHERE, Ma?” asked Jay.

Catherine Leno found Disneyland too serious a place for jokes

Jay’s father, Angelo Leno, was an Italian-American insurance salesman, proud of working hard, and touchy about being slighted. The Lenos were neither reserved nor frugal. When Jay ate with the Leno side of the family, there were great heaping plates of spaghetti and meatballs. Jay’s mother, like a good Scot, counted the meatballs still left on people’s plates when dinner was done, and pronounced: “What a waste!”

Jay’s parents, Catherine and Angelo Leno

Jay loved to prank his parents. When he was seven or eight, he’d slip away from his mother at a department store, find the manager and say he couldn’t find his mother, could they page her. “Paging Catherine Leno. Catherine Leno, come to the front desk to collect your child…” And Jay would be laughing as his mother came charging up.

When he was 14 years old, he got a 1934 Ford, and began working on it. But he didn’t have a license to drive it. One day when he was 16, he was biking in Andover, when his friend Louie came driving up in a nice car, with a girl riding shotgun… Jay felt a surge of jealousy.

Louie looked out the window and said: “Hey, man, you goin’ uptown?”

Jay said, “Yeah, I’ll meet you there!”

Louie and his girl roared off in the car. By the time Jay got to the meet-up spot, Louie and the others were gone.

Jay moaned, “Man, I’ve got to get my license!”

The teenage Jay Leno

When it was time for college, Jay went to Bentley College and signed up for Accounting classes. A dyslexic accountant. He lasted one semester before dropping out.

Then someone told him about Emerson College. There he found a sympathetic administrator and, as an informal application, did a comedy routine. After all, there’s a time to be funny and a time to be serious. Being serious hadn’t worked out at Bentley College; maybe now it was time to be funny. The Emerson College administrator laughed at Jay’s jokes and thought his humor and moxie were a better indicator of potential than his weak transcript. After exacting a promise from Jay that he’d work hard, the guy accepted Jay at Emerson.

Jay got a degree in speech therapy, but poured his time into starting a campus comedy club and doing stand-up. His father was secretly proud of Jay but not inclined to show it. And Catherine Leno was openly skeptical of Jay’s imagining any sort of career in comedy. She said again and again, “Jay, we’re not SHOW people.”

Jay took the same approach he had at school. Forget about your trouble reading. Show up — do the stand-up gigs. Listen very carefully to comedians. Soak in the rhythms, memorize the punch lines. See humor whenever it shows itself. It might be in a heckler’s taunt or in the intro from the emcee. You’re not that funny; so outwork the other comics.’ For years, he worked 210 nights a year. Today he will say “The key to life is low self-esteem” and he’s only half-joking.

Leno did a lot of stand-up in small clubs before his career took off

The low point in Leno’s career was being in New York without enough money to afford a place to stay, sleeping in an alley off 44th Street and 9th Avenue, near the Improv.

Another tough time was when a girlfriend told him she was bringing her father to one of Jay’s stand-up shows. Jay had met the man only briefly but knew his face and kept looking over at him during the show. No matter how much the rest of the audience laughed, this guy never cracked a smile. Only after the show did Jay learn the guy had Bell’s Palsy.

In 1976, at the Comedy Store in Los Angeles, Leno met a woman named Mavis, and they got married. They’ve never had children, or wanted to. Mavis is a serious professional, a feminist and a philanthropist. Jay loves it when show business people meet her, expecting “Mrs. Jay Leno” to be an airhead, and find her extremely well-informed.

Jay and Mavis

He kept traveling the comedy club circuit and noted that stand-up was becoming a little more lucrative. He could tell that stand-up was becoming “a thing” because the clubs he played were getting cuter with the names. He’d started at clubs with names like The Boston Comedy Club. By the late 1970’s, they started naming clubs things like “Jokers” and “Giggles” and “Ho-Hos.”

One of Jay’s best pranks on his father took years to pull off. Jay was all grown up and doing comedy in L.A. when his mother said his Dad had fallen off the roof while doing some maintenance work, and was in the hospital. Jay flew to Boston, drove to the hospital, convinced them to give him a white coat and a stethoscope, and then entered the room where a grouchy Angelo Leno was recuperating. Disguising his voice and talking to Angelo with his back turned, Jay asked gruffly: “What’s wrong with you?”

Jay did his own version of a hospital visit to a loved one

His Dad said stoically: “I got this thing…”

Jay moved in for the kill, saying in a voice thick with disgust, still with his back turned: “We get a lot of guys like YOU in here.”

Angelo said, “What do you mean ‘guys like ME’? I don’t like your tone, fella.”

Jay said: “We get a lot of guys like you, never worked a day in their life, looking for a free meal and a bed.”

Suddenly, his back still turned, he could hear his dad charging him, screaming, “You son of a bitch!”

Jay turned and said, “Pop, it’s me!”

On March 2, 1977, Jay was on “The Tonight Show” with Johnny Carson for the first time, and that was a great night. (Actually, Jay says your first time on “The Tonight Show” is like your first time making love. It’s over fast, you don’t perform very well — and you can’t wait to do it again.) In that sense, Jay was not very good his first time on national TV. But just the fact that Johnny Carson endorsed him, and put him on the show made it much easier for Jay to get bookings at the top comedy clubs.

From the start, Leno was as careful as a Scot with his money, and as soon as he could, he lived on his comedy income. All the money he made doing other jobs he put in the bank.

In 1986, Leno began guest hosting for Johnny Carson on “The Tonight Show.” And in 1992, NBC chose Jay to take over the “Tonight Show” Leno’s friend and rival David Letterman was bitterly disappointed that Letterman hadn’t been chosen to succeed Carson — and so, reportedly, was Carson.

Leno got the gig replacing Johnny Carson, surprising David Letterman — and Carson

Leno didn’t want to talk about what he or his representatives had done to secure the position as Carson’s successor. His job was to be funny, and backstage maneuvering in showbiz isn’t funny. He made the show’s title “The Tonight Show With Jay Leno” instead of “The Tonight Show Starring Jay Leno.” A little bit of Scottish reserve, a little touch of modesty in Los Angeles, kingdom of glitz. Still, when Jay’s mother came out for a visit, she said “Why do you have your name all over everything?”

In 2004, NBC announced that in 2009 Conan O’Brien would take over “The Tonight Show.” Leno even said on the air in 2004, “Conan, it’s yours! See you in five years, buddy.” But in 2009, the sharp elbows appeared and Leno decided he didn’t want to give up the show to his “buddy.” NBC tried to keep both Leno and O’Brien happy, and wound up losing both of them. Conan said on TV: “I just want to say to the kids out there watching: You can do ANYTHING you want in life…. Unless Jay Leno wants to do it, too.”

Both David Letterman and Conan O’Brien excelled at self-mockery, reveled in being weird, and got the audience to come along with them. Leno had a broader, blander appeal. His strategy for popularity was simple. Combine all the different kinds of jokes in the monologue. A sharp political joke, then a corny joke. A dig at the Democrats followed by one at the Republicans. Something for everybody.

NBC executives seemed nervous that Conan O’Brien’s appeal wasn’t broad enough

The “Tonight Show” audience is a friendly one; part of what they’re paying for when they buy tickets is the little thrill of being part of something on national TV. And, of course, Leno had a staff of writers to help with the jokes. But the schedule was relentless. Jay needed 12 minutes of comic material every day that he could go on national TV with. Most people can have a lousy day at work, come home and go to bed. Leno always had a show to do. He’d shrug and say: “It’s only work if you don’t enjoy it.”

He’d relax by going to his garage and working on his vehicles. By 2016, he had about 200 cars and 90 motorcycles. (“One woman and 200 cars is cheaper than one car and 200 women.”) When people ask him how many cars he has, he will say, “You sound like my wife.”

He knows that people in Los Angeles show business circles will tell you ‘You’re great, you’re great’ — even when you’re not. So touring is something he likes to do for the challenge of it. There, writing and performing all his own stuff, he finds out how funny he really is. The audiences are much tougher; they may have bought tickets to the club but probably not to see Leno. No one is there just hoping to be shown on television.

Leno is acutely aware that he has a skill — making people laugh — that might have gotten him killed at an earlier point in history. He figures if he’d been caught during the Crusades making the soldiers laugh when they should have been plundering, he’d have ended up being tortured on the rack. Yet because he lives now, he’s been able to make a fortune. Life is funny.

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Andrew Szanton

Andrew Szanton is a memoir collaborator based in Newton, MA. If you or someone you know wants to tell a life story, contact him at aszanton@rcn.com.