Late-night funnyman David Letterman was hardly a barrel of laughs off the air.
A new biography of the now-retired talk show host portrays Letterman as more self-loathing than self-critical — and an often miserable man who inflicted his pain on his staff.
“He was never truly comfortable unless he was seething with unhappiness at something,” one longtime writer told author Jason Zinoman in “Letterman: The Last Giant of Late Night.”
In fact, few of the acerbic Letterman’s close colleagues sang his praises to Zinoman.
Letterman’s demeanor soured after July 1995, when his CBS front-running program dipped to second place behind “The Tonight Show” with former friend-turned-enemy Jay Leno.
Viewers flipped to NBC when Leno landed an interview with actor Hugh Grant, fresh off his arrest for soliciting a hooker improbably named Divine Brown.
Many never returned, curdling Letterman’s on-air persona.
He became more openly caustic as his comedy took a sadistic turn. One night, after his “Late Show” was whipped in the ratings by both “The Tonight Show” and “Nightline,” his rage visibly surfaced.
A comedy bit called for a life-size Letterman doll to sit in the guest’s chair. Seemingly on the spur of the moment, Letterman punched the doll — to much audience laughter.
The laughs continued as he landed a few more blows. And then the 580-seat theater went silent when Letterman fell into a frenzy of punching and slapping his plastic alter ego.
Obviously, something was wrong with Dave.
“People don’t understand why you’re behaving the way you’re behaving,” said Rob Burnett, a trusted colleague and the head of Letterman’s Worldwide Pants production company, in a candid chat with his boss.
Letterman’s anger wasn’t all directed inward, and he became upset with pretty much everyone on the show.
Burnett returned as executive producer, but things became strained. His unique ability to manage his boss’ dark moods ended with a “falling-out,” according to Burnett.
Their relationship eroded to the point where they were barely speaking. According to a veteran producer, “everything changed after that.”
A veteran staffer who served under Letterman through both his late-night shows observed that getting close to the boss was perilous: “There comes a moment when he turns on you.”
The tale of Tim Long, one of several head writers hired during the show’s run, was typical. Unable to deal with the host’s constant rejections and dark moods, Long took to chewing Coke cans — and swallowing pieces of tin.
Even the famously mellow Paul Shaffer lashed out at Letterman one night when Todd Rundgren sat in with the band.
Letterman kept pushing and needling, trying to get Rundgren to do more than the one number done in rehearsal.
“The cat flies in to do us a favor and you just want what you want,” Shaffer yelled at his boss.
It embarrassed Shaffer so much the moment was cut from the show before airing, even though Letterman said he was fine with it.
The irony: Letterman was miserable even when his ratings put the show at No. 1 in late-night viewers. In 1993, he walked away from NBC after the network chose Leno to succeed Johnny Carson, taking the 11:30 p.m. slot on rival CBS for his “Late Show With David Letterman.”
CBS offered Letterman a then-record deal with a $16 million annual salary. The payoff was immediate as Letterman seized the ratings lead against the once-invincible “Tonight.”
Yet Letterman remained miserable. “He always complained from the very beginning,” recalled one producer.
Things went downhill from there.
“It got worse when he went to CBS,” recalled Shaffer. “Any flaw, minor flaw, he exaggerated. He was most uncomfortable at No. 1.”
Comic Rich Hall, a writer for Letterman’s NBC show, was floored by the host’s new, abrasive nature when he appeared as a guest. Hall followed actress Andie MacDowell, who had just flopped in her segment. Before the cameras came on, Letterman leaned over and snarled, “How’d you like to be married to that c—?”
What the author calls Letterman’s “ferocious fear of failure” was there from the first.
The feeling of foreboding was exacerbated by the 1980 cancellation of his NBC morning show, “The David Letterman Show,” within months of its debut.
His girlfriend at the time and for years to come, Merrill Markoe, was a brilliantly inventive comedy writer and instrumental in shaping the show.
Markoe, who rarely comments on Letterman publicly, told the author about the resulting fallout.
“If it weren’t for you and your crazy ideas,” Letterman shouted at her on the street, “I’d still have a talk show like John Davidson!”
It’s a comment funny only in retrospect.
Markoe became head writer on NBC’s “Late Night With David Letterman” from the first show in 1982 — and suffered for that, too.
Every night after the show, an agonized Letterman would lock himself in his office with Markoe.
“The last 10 months have included a nightly discussion about what a failure we are,” she once noted.
In those days, the acid-tongued Letterman would hang out, trading barbs with the writers. His targets learned not to return in kind, as the hurt would show on Letterman’s face.
“He was very sensitive,” says Barbara Gaines, a producer who remained with Letterman until his 2015 retirement.
By the end of the ’80s, Letterman was the king of hip and cool. He now smoked cigars and assumed “a statelier air.” Notably, he no longer made a show of despising celebrities, as he had for a decade.
When Barbara Walters booked him as a guest interview on one of her specials, he walked around the office openly expressing his admiration for her.
“What happened, Dave?” asked head writer Steven O’Donnell.
“They are like my peers now,” the host told him.
It was during that era that Letterman started abruptly turning on longtime, trusted colleagues. Barry Sand, a producer and ally since the morning show, suddenly could do nothing right.
After a guest canceled at the last minute, Sand scrambled and was able to book Mel Gibson — then at the height of his fame. Letterman turned on the producer and snarled, “Who the hell wants Mel Gibson? I don’t want Mel Gibson.”
He opted instead for Kamarr the Discount Magician. Sand was soon gone.
In the rush of his success, the formerly prudish Letterman switched up his persona, booking “leggy supermodels” as frequent and welcome guests.
The phrase “leggy supermodels” was funny, but Letterman’s leers came off as sincere and appreciative.
Boorish advances became his signature. Sitting next to Jerry Hall, whose breasts exploded from her dress, he openly enjoyed the view.
“I get the awful feeling I may have overinflated my tires,” quipped Letterman.
On one cringeworthy show, he sucked on a strand of Jennifer Aniston’s hair.
Zinoman writes that after a time, the satire faded away to show the bits for what they were — a rich and famous man indulging his fantasies.
“As he got older, Letterman increasingly played the horny creep,” he writes.
By the time he was an eminence grise on CBS, he became “crudely sexual” in his interviews. The camera would slowly pan over the legs of Aniston or Gwen Stefani as he delivered lascivious comments.
“He seemed like a pervy old man at times,” says one of his head writers, Eric Stangel.
Even before the 2009 scandal when an affair with an assistant exposed Letterman to an extortion try, the host interacted infrequently with most of the show staff.
The only trusted colleagues were those who had worked with Letterman for decades — at least, those left standing.
Letterman just couldn’t bring himself to talk to people.
It seems, though, that after a year and a half in retirement, Letterman is now eager to chat.
In an interview with New York magazine, Letterman claims his son, Harry, 13, doesn’t like being in public with him.
Not because of his snow-white mountain man beard, but because he talks too much to everyone.
Letterman might have been kidding. Or not.
