Say Hello to David Letterman’s On-Air Sidekick, Biff Henderson!

Photos by Stefan Radtke

David’s Letterman’s longtime stage manager may be retired now, but he’s as popular and funny as ever. 

Biff Henderson is a regular at the City Limits Diner on Central Avenue. He comes here after services at Grace Episcopal in downtown White Plains, the historic stone church that sits in the glacial blue shadow of The Ritz-Carlton towers. He and his wife, Carolyn, a retired special-ed teacher, bought a house in Greenburgh decades ago because it reminded Biff of his native Durham, NC. They raised two now-grown children here, James and Celeste, who’s mother to granddaughter, Sydney.

Everybody at City Limits knows Henderson, from the hostess to the waiters. The place is packed on a Thursday morning, and between bites of eggs Benedict, Henderson flashes his familiar, gap-toothed smile at people making eye contact. When a man stops to shake his hand and tell him he’s a big fan, Henderson says “Thank you!” looking simultaneously pleased and perplexed, as if after almost 35 years behind the scenes and on the air with David Letterman, he still can’t quite believe total strangers know who he is.

Granted, these total strangers are on the more grown-up side, middle-aged folks who stayed up past midnight in the ’80s and ’90s to catch Letterman’s new Top 10 List, Chris Elliott’s surreal impersonations, and stage manager Biff Henderson’s latest goofy stunt or interview. Henderson was the one with the headset, the liaison between the host, crew, celebrities, and the control room — when he wasn’t driving a golf cart through jars of mustard or reporting from the Super Bowl, that is. Not for nothing, but Rolling Stone rated Henderson No. 5 on a list of Letterman’s top-10 sidekicks.

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Henderson is retired now, but not by choice. The best stage-manager gig ever ended on May 20, 2015, when Letterman signed off after more than 30 years, making him the longest-running late-night talk show host in TV history. Just weeks before the star-studded final show, Letterman called Henderson “a friend…and a real fixture on the show — and like so many other fixtures of this show, more beloved, really, than me.”

A youthful 71, Henderson chalks up his good fortune to “faith and destiny. I think things that come true were in the plan for you…. If you don’t have faith, if you think you’re going to do this all on your own, I don’t know about that.”

His given name is James Jackson Henderson Jr., but his mother’s friend had a dream she would have a baby named Biff. So “Biff” he has been ever since. His father was a successful businessman, bank chairman, and head of the Durham Housing Authority. Henderson grew up in the segregated South, when blacks lived a mirrored life to whites, with their own neighborhoods, schools, even theaters — what Henderson calls “separate but equal.” He had a comfortable middle-class life.

As a young man, Henderson was a serious tennis player. He took it up at age 6 and was winning national tournaments by the time he was 10 on the American Tennis Association Tour, a junior league for black players. (Another young player, named Arthur Ashe, stayed at his home while playing in Durham.) Henderson played No. 1 singles at Hillside High School and attended Hampton University in Virginia, where he played for one year and quit. “I hit a wall when I was in college, and I hated the sport, so I didn’t play for years.” He took it up again as an adult, playing on Greenburgh public courts.

After college, Henderson was drafted into the Army. In 1968 and ’69, he spent more than a year with an artillery patrol unit stationed at Dong Ha Combat Base in Vietnam. He didn’t talk about the war until recently. “It was rough; that was the worst time in the war,” he says. “It was nothing I volunteered for, but there’s nothing I regret having done.”

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Upon returning home, Henderson got a sales job with American Airlines in Nashville. He wanted to move to New York City, so he sent his resume to a few places, including Hertz, and in 1970 flew up for some interviews. And here is where destiny comes in, because after the interview in Rockefeller Center, he had to use the bathroom, badly.

“Behind me came a voice: ‘How are you today, young man?’ I washed my hands, turned around, and there’s this very distinguished-looking man with a bow tie, a dustpan, and a broom. He was Gene Sanders, a janitor. We started talking, and he said, ‘What brings you to NBC?’ I told him I didn’t know I was in NBC. He said, ‘I want you to meet someone.’”

That someone was a sales executive at NBC. In a few years, Henderson went from selling radio airtime to working in production and filling in as stage manager for employees on vacation. He did it all: game shows, space-shuttle launches, The Today Show. In the summer of 1980, he was assigned to a morning show with an up-and-coming comic named David Letterman. “We got along well.” So well that one day, when the time came for the opening monologue, Letterman pushed Henderson, a behind-the-scenes guy, out in front of the camera.

Henderson with wife Carolyn at their Greenburgh home

“I walked out for the monologue. I thought: This is nothing; I can read cue cards like anybody else. So I went out there and started telling jokes. Dave came on and pushed me out of the way. Back then, everything Dave did was very of the moment. He thought: This is going to be funny, and it was.” In 1982, after Henderson joined the comic on Late Night With David Letterman, “he started sending me out in the street, doing stuff, and next thing I know, writers are coming along with crazy ideas: Let’s go across America; let’s go all all over the world! With Dave’s show, anything could happen at any time.”

In 1991, something big did happen: NBC picked Jay Leno over Letterman to take Johnny Carson’s time slot. Letterman decamped for CBS, taking Henderson with him. By the time the curtain came down in 2015, Henderson had spent half his life alongside Letterman, to whom he remains intensely loyal.

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“When the show ended, I was not mentally ready to retire,” recalls Henderson. “I was enjoying what I did. It was work, but it was fun. I know he announced it a year in advance, I knew the show was going to end, but I wasn’t ready. It’s going on just over two years now, and I’ve adjusted.”

Henderson keeps his hand in the game with cameos on Jimmy Kimmel Live! and celebrity appearances. A left-knee replacement has curtailed his tennis game, but “it’s not the leg I hurt on the show,” he says, referring to the 2010 injury where he fell off a stage, catching a football thrown by Letterman.

A man of deep faith, Henderson is very active at Grace Episcopal as an usher and lay reader. His pastor, Father Richard Kunz, describes Henderson as “low-key, funny and self-deprecating. He’s a great person to have around: reliable and generous.” Henderson is funny almost without trying to be. As longtime Late Show director Jerry Foley puts it: “I think there’s some Yogi Berra in Biff. I don’t think he understands how funny and insightful he is.”

Henderson last saw Letterman in October, when he made an onstage cameo as the talk show host received the Kennedy Center’s Mark Twain Prize. Letterman will be returning to the host’s chair for a six-episode interview show on Netflix, but Henderson is not sure he’ll get the call. He’ll leave it up to faith and destiny. “I’ll tell you this much: I’ve been blessed, and if that’s what’s supposed to happen with Dave again, so be it.”

Ossining resident Dana White, a frequent contributor to Westchester Magazine, spent far too many late nights watching Henderson’s antics with David Letterman.

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