Trouble began for David Letterman over a prostitute hanging out near Sunset Boulevard. It was June 27, 1995 and his “Late Show” program was number one in ratings. But it wasn’t Letterman who was attempting to procure the sexual services of Divine Brown. It was actor Hugh Grant who solicited the hustler and was arrested for allegedly engaging in lewd conduct in a police sting.
Fortunately for Letterman’s nemesis, Grant was scheduled to appear on Jay Leno’s “Tonight Show” just two weeks later. Media coverage exploded and the press was begging to attend the Monday evening taping with Grant. NBC arranged to hook reporters around the country up to a live audio feed just in time. Leno wasn’t going to let this opportunity go. This was his chance to take over the top spot and he did.
“OK, question No. 1: What the hell were you thinking?” Leno asked.
“It’s not easy explaining,” Grant answered. “People have given me tons of ideas on this one, from ‘I was under a lot of pressure, I was lonely, I fell down the stairs when I was a kid’ . . . but I think it would just be bollocks to say anything like that…I’m sure I would be enjoying this as much as everyone else, but it’s horrible when you’re on the other end.”
Leno was on his game. When a female in the audience asked if she could sit next to Grant before the taping started, Leno replied, “I think we saw what happened last time someone asked him that.” Then, when discussing about the hot weather the crowd had to endure while waiting in line, he said, “The audience was sweating worse than our first guest.”
Letterman’s former staff members told author Jason Zinoman that when his show dipped down to second place, their boss’s behavior turned from moody to bad. It never recovered.
Looking more like a white-bearded John Malkovich than he does Santa Claus, the retired Letterman is now approaching two years off air. At 69, Letterman has kept much to himself, but is about to be hit with a tell-all book, “Letterman: The Last Giant of Late Night,” by Zinoman. It promises to reveal Letterman as one miserable soul.
“He was never truly comfortable unless he was seething with unhappiness at something,” one Late Show writer revealed to Zinoman. He began taking his anger out on anyone near him.
“People don’t understand why you’re behaving the way you’re behaving,” said Rob Burnett, chief of Letterman’s Worldwide Pants production company. After a “falling out” their relationship was never the same.
The New York Daily News reports 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.’”
Zinoman writes about the show’s bandleader Paul Shaffer on the air clash with Letterman. Musician-singer Todd Rundgren sat in with the band one night while Letterman continued to harass him to do another song besides the one he did in rehearsal.
“The cat flies in to do us a favor and you just want what you want,” Shaffer yelled at Letterman.
The Daily News reported the incident “embarrassed Shaffer so much the moment was cut from the show before airing, even though Letterman said he was fine with it.”
“It got worse when he went to CBS,” said Shaffer. “Any flaw, minor flaw, he exaggerated. He was most uncomfortable at No. 1.”
“He was very sensitive,” says Barbara Gaines, a producer who stayed on with Letterman until his 2015 retirement.
Lately Letterman has been granting interviews and appearing on talk shows, perhaps an effort to circumvent the upcoming book. During Steve Martin’s and Martin Short’s touring show, A Very Stupid Conversation, Letterman walked on stage at their Majestic Theater performance in San Antonio to put down Donald Trump. But despite Letterman’s disgust, Trump won.
The book covers Letterman’s career from Indiana to his retirement and portrays him as a hypochondriac who kept “The Merck Manual” near his desk. Zinoman writes that at one instance Letterman said he had “heart tumors.”
“He spent weeks obsessing about mercury fillings in his teeth, calling in doctors for consultations,” the Daily News reported. “Another time, he literally traveled the world looking for a cure for dizziness that he imagined was a case of disequilibrium; after two days of examinations, a doctor in Munich finally convinced him nothing was wrong.”