fb-pixel Skip to main content

As Letterman retires, so does Belmont joke writer

Belmont resident Bennett Alper said hearing his jokes on television “is a high.”Dina Rudick/Globe Staff

BELMONT — Bennett Alper gets out of bed every day at 5 a.m. and shuffles to his computer. Before he’s even had coffee, Alper scans the day’s headlines and dashes off a dozen jokes.

Alper has submitted jokes to David Letterman and Jay Leno for over two decades. The pay is meager and the prestige strictly personal, but the thrill of watching Dave or Jay deliver one of his punch lines has been enormous.

“It’s a high,” says Alper. “That’s what it is.”

It’s a ritual that’s about to end. When Letterman signs off for the final time next week, Alper’s career as a wisecracker is over.


Alper is a vestige. He and other freelancers who for years have faxed or e-mailed their jokes every morning are fading from the industry as the older generation of late-night TV hosts step down. Some shows, like “The Tonight Show with Jimmy Fallon,” no longer accept gags from freelancers. Writers now use Twitter to find an audience for quips that were the hallmark of late-night monologues.

Since selling his first gag to Leno in 1992 — a zinger about then-presidential candidate Paul Tsongas wearing a Speedo — Alper has rarely taken a day off, jotting down jokes in a tiny spiral notebook even while on vacation. So what if most of them never made it into a monologue?

“You do this for the love of it,” he says.

But Letterman’s last show airs Wednesday on CBS, and Alper admits he’s relieved. At 61 and newly married, he’s ready for a change. Sitting on the porch of the apartment he shares with his wife, former Boston Herald TV critic Monica Collins, Alper says he wants to try being funny in long form. He’s working on a book tentatively titled “Living Inside My Head: An Introvert’s Home Sweet Home.”


Writing one-liners is not how Alper makes his living. That would be impossible. The dozen freelancers who submit jokes to the “Late Show” are paid $75 for each one used. On average, Alper says, Leno told one of his jokes every two weeks, and Letterman even less than that. You do the math.

“The most famous monologue freelancer we had was Johnny Carson, who faxed jokes to Dave the last five years of his life,” longtime Letterman staff writer Bill Scheft said in an e-mail. “A couple dozen aired, which means Johnny made a cool $1,800.”

Alper has instead paid the bills as a technical writer for websites, composing the humorless, humdrum language for Help menus. But if someone asks what he does for work, he always says “comedy writer.”

“In my heart, that’s what I do,” says Alper.

It’s all he ever wanted to do. He tried college — three times — and could never fathom an office job. So in his 20s, Alper, who grew up with six siblings in Rehoboth, decided to move to Los Angeles. He bought a book that listed comedians’ agents and mailed out batches of jokes, getting reams of form rejections in return. Except from Bob Newhart, who replied with a handwritten note.

“I liked your material. I thought it showed a great deal of promise,” Newhart wrote. “Having received hundreds of material submissions, I have not been able to say this too often.”

Alper returned to Boston encouraged.


“It was the first time someone said to me, ‘You know how to write,’ ” he says. “It was the first indication I could do this.”

A letter to Bennet Alper from Bob Newhart. Dina Rudick/Globe Staff

Alper is not a natural performer or raconteur. Whatever the charisma gene is that leads comedians to get on stage, he doesn’t have it. In person, Alper, who’s bald and beyond unassuming, comes across as a friendly milquetoast, the opposite of funny. He has a hard time reading one of his jokes aloud without flubbing the punch line.

“He’s the last guy you can demand to be funny,” says his wife, who met Alper when she responded to a personal ad that read: “Man who has everything seeks penicillin.”

In 1992, after reading a story in the Globe about Leno taking over as host of the “The Tonight Show,” Alper mailed Leno’s manager a sample of his work. (By then, he’d sold several jokes to Joan Rivers — for $10 apiece.) A few weeks later, he got a reply.

“It said, ‘Here’s a contract, fill it out, and start sending us stuff,’ ” says Alper.

He quickly figured out that Leno, like Carson, enjoyed riffing on the news, whether it was politics or pop culture. But on a normal day, Alper was told, the host and his staff looked at 900 jokes, so getting something into the monologue wouldn’t be easy.

He took that as a challenge, beginning the routine of waking every day at dawn to read the news and write one-liners. By 8 a.m., he would churn out 15 bits and fax them to Leno’s writers. Because he went to bed early, Alper would tape “The Tonight Show” and watch in the morning to see whether one of his jokes made it.


When Leno went off the air 18 months ago, Alper figured he

was done. But a friend gave him an e-mail for the “Late Show.” He says writing for Letterman is not like writing for Leno. Letterman tells fewer jokes in the monologue — 12 compared to 25 — and he never delivers a line as it was written.

“You write for these guys for a while, you know where the joke is,” he says. “But you write a joke for Leno, and it’s written well, that’s the way he tells it. With Letterman, he just kind of grabs the idea.”

There’s been little glory because freelance joke writers are anonymous. Alper has never met or spoken to Letterman, and only talked to Leno once in 20 years, in 2011, after Alper’s father died.

“I felt about as bad as you can feel. My father was my biggest fan,” he says. “It was Jay. He knew who I was. And he didn’t mention a thing about work. It was just like your friend
calling up.”

Alper says the end of Letterman is bittersweet.

He’ll probably still write or tweet a few jokes every day — “He needs this like flowers need the rain,” says his wife — but he’s looking forward to being funny for himself.


“I do this willingly, but you do feel like you’re doing it for practically nothing for a multibillion-dollar corporation,” says Alper.

“That’s the hard part for me and why, at this point, I’ve had enough.”

Fallon doesn’t accept freelance material, but there is one person Alper would like to write for.

“I’m going to pursue [Senator] Elizabeth Warren,” he says. “I saw her telling some jokes, but they weren’t that good.”

Mark Shanahan can be reached at mark.shanahan@globe.com. Follow him on Twitter @MarkAShanahan.