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Despite his kids-in-the-hall casualness around the office, Letterman is a fiercely driven perfectionist who controls virtually every detail of his show. "There's more tension than any place I've ever worked," says an ex- staffer. Letterman rejects reams of material submitted by his team of a dozen writers, and he crosses off potential guests by the score. "We'd hand in a list of 50 guests, and he'd say no to 48," says a frustrated former booker. He is also notoriously moody and has last-minute pangs of self-doubt. "In the makeup room five minutes before the show," says head writer Rob Burnett, "Dave will suddenly say, 'This bit is not going to work.' Sometimes he needs to be almost pushed in front of the camera." After the show, he typically replays the videotape and broods about mistakes or bits that misfired.
"He's incredibly insecure and very self-torturing," says Merrill Markoe, his former girlfriend, who helped create Late Night, devised such popular bits as Stupid Pet Tricks and wrote for the show until 1986. "He doesn't ever reward himself for a job well done. He always feels that he screwed up. In fact, in all the years I knew him, I never once heard him say he thought something went pretty well. The most he ever gives himself is remarks like, 'Well, I guess that stuck to the tape.' "
Markoe and Letterman split up five years ago and no longer speak. Letterman expresses no bitterness and praises Markoe as "the smartest, funniest woman I've ever been around." Markoe, who is now writing books, says she hasn't watched Letterman's show since the breakup and "won't even talk to people about working on another late-night show. I have no interest in helping any other white man in a suit do an inventive show. Let them all find their own damn inventive shows."
If women staffers describe Letterman's program as a boys' club, it is not just because only one of the show's 12 writers is female; it is also because the off-camera Letterman is much like the on-camera, prank-playing fraternity boy. Staffers recall the chaos that ensued during an office celebration several years ago, when he set off a flare in Morton's office and triggered the building's smoke alarms. A couple of weeks ago, Letterman challenged head writer Burnett to an oyster-eating contest: $150 if he consumed 50, $10 for each one thereafter. (Burnett wolfed down 60.)
Letterman's outside interests mostly involve sports. He jogs and swims (more of the latter since he injured his neck in a car accident two years ago), plays basketball and went to the All-Star baseball game in July. His No. 1 passion is auto racing. Letterman keeps a collection of foreign sports cars in an airplane hangar in Santa Monica, pores over British racing magazines and takes a different friend each year to the Indianapolis 500, part of his campaign to show that the sport is "more than cowboys in cars going as fast as they can." Racing has a nostalgic appeal for Letterman, who grew up in Indianapolis. "I can remember as a kid going out to the speedway with my uncle to watch time trials for the race," he says. "I loved those days."