Even as Letterman got off to a great start at a new network, his legendary self-loathing remained; he’d apologize to staff members on his way out the door, or tell reporters that the last time he felt good about himself was a Tonight Show appearance he made in 1978. By then, he’d taken up with Regina Lasko, now his wife, who had been a production staffer on Late Night before heading to Saturday Night Live for a short time. Lasko, like Markoe before her, had a great mind. Dave, it seemed, had a type: women who impressed him intellectually, who somehow had his number. They were not necessarily the obvious choices. “You can look at these women and see how they look,” says one former staffer. “You see he’s going for personality as well, but I think he’s also going for easy targets. He’s not setting himself up for rejection. He’s not going to ask the head of the cheerleading team to prom. He’s going to ask the head of the band or something.”
Letterman kept to a small circle of friends, most of them buddies from his L.A. comedy days. Former staffer Laurie Diamond once said she regularly fielded calls from ex-girlfriends hoping to reconnect, but he ducked them. And as the years have gone on, he has cut off his contact with more and more of the people around him at work. There is no more playing softball with the staff, no more kibitzing all day with writers. “After 29 years and thousands of episodes, the process has evolved to where Dave comes into it a hair later than he used to, but he remains as focused as ever on every last detail of the show,” says Rob Burnett, the former Late Show head writer who is now the head of Dave’s production company, Worldwide Pants. To the rank and file of the show, however, Dave is almost a nonentity now. “He and his assistants are literally walled off from the rest of the staff, behind a glass door,” a former staffer says. “There is just no contact.” His absence has brought a new level of palace intrigue to the Ed Sullivan Theater. “There’s a level of mind games and chess that goes on, starting from the top down. They rule by fear. You don’t want to make Dave mad or so-and-so mad, so you better do a good job. Everyone there is scared of their shadow all the time.”
The staff, meanwhile, has swelled in number. Because of the show’s prestige, and because the company is good to its employees, people get promoted and new people come in, but few leave. Yet the show only needs a certain number of people on any given day. “They keep dividing the show into smaller and smaller sects,” says the former staffer. “It’s like tribal warfare. It can’t function effectively.”
The lack of access to Dave makes being one of his personal assistants one of the most appealing jobs on the show. Anyone in a far-flung department who needs a question answered by Letterman knows to go to his assistants now, and not an executive producer. “The problem,” the source says, is that “they’re cut off from the outside world. They only have each other to hang out with. Dave has this very paranoid vision of the world where they shouldn’t be giving information to anybody else and they shouldn’t be associating with anybody else. And so they start to feel very, very loyal, and very trapped. When someone has seven assistants, each one of them does one thing. One presses the red button, one presses the green button, one presses the yellow button.”
Stephanie Birkitt joined the Late Show in 1996, first as an intern and later as an assistant to Letterman. With her sharp wit and unaffected manner, she fit the mold of the kind of girl he felt comfortable around. “She was smart,” says a source who knows her. “And she didn’t have any sense that this was the greatest thing in the universe and we’re doing God’s work here.” She was a hard worker and a go-getter, eager to appear on the air in whatever wacky capacity the show needed. (Within a day of Letterman’s announcement, people were YouTubing videos of Birkitt’s appearances on the show and scouring them for hints of the affair.) Birkitt “liked being part of a team,” says the source. “The job was her social life as well. She was one of the people you saw more frequently.” Birkitt, the source says, wasn’t “this vixen, slutty, hitting-on-your-husband kind of girl. She never dressed or acted inappropriately.” But after a while, there were rumors that Dave used to get in the car at the end of the night and say uptown or downtown. Downtown meant his loft in Tribeca. Uptown would mean Birkitt’s.