41. A CBS Producer Was The Culprit
The blackmailer turned out to be Joe Halderman, a producer on the CBS show 48 Hours. Apparently, he should have watched more of his own show, because the cops caught him pretty much instantly. He pleaded guilty to all charges and served six months in jail, plus probation and community service. His plan had blown up in his face—but even if he didn't get the money, Letterman still had to deal with the fallout.
42. He Slept With Several Younger Staffers
After years of sneaking around, Letterman finally admitted to having several affairs with women who worked on his show. He carried out a relationship with the show's intern, Holly Hester, despite the massive difference in their ages. However, his most scandalous affair was with his long-time personal assistant, Stephanie Birkitt. That's where the details of Letterman's cheating start to get really wild.
43. He Made His Ex Work For His Mistress
Letterman's breakup with Merrill Markoe wasn't exactly friendly, but after years of silence between them, she finally got a call in the mid-2000s. Letterman implied he wanted her to come do some on-camera bits for the show—but in reality, he had something far more twisted in mind: He wanted Markoe to write bits for a young intern named Stephanie Birkitt.
Markoe wouldn't realize what was really happening until much later: Letterman had brought his ex-girlfriend back to write jokes for his mistress.
44. One Affair Cost Him Everything
The affair with Birkitt was eventually what sealed Letterman's fate. Birkitt didn't only work on the Late Show; she had another gig: 48 Hours. In fact, she actually lived with Joe Halderman in the months leading up to the blackmail attempt. Halderman had access to Birkitt's personal diary and emails, and he used them to try and extort Letterman.
45. He Made Everyone Else Miserable Too
Letterman was unsurprisingly miserable after his affairs came to light, but at least he managed to make life miserable for everyone around him too. After every taping, Letterman would gather all of his writers to go over every aspect of the show they'd just finished. Then he'd bring writers and producers back to his office to just...talk. They'd talk about anything for hours on end. One staff member described it as a hostage situation.
All because the prospect of going home and facing his wife terrified him.
46. He Wasn't A Great Boss
To be fair, it's not like the Late Show was the most fun work environment to begin with. Although Letterman was close with his writers in the earlier years, he'd been doing the show for decades. He eventually became aloof and distant, and he came to dread even speaking to his writers. He spent almost all of his time hidden in his office and made the writers speak to him through Steve O'Donnell, the head writer.
Eventually, the writers had a saying: “You might get to meet him when you leave.” But that's not the worst of Letterman's behavior as a boss.
47. He Was Passive-Aggressive
Letterman was an infamously passive-aggressive boss. I guess the whole "holed up in his office never speaking to anyone" thing might've been a hint. He hated conflict, and he would never fire anyone. Instead, he would just completely freeze them out of the show until they eventually got the message. That's a horrible way for anyone to lose a job—but for longtime producer Barry Sand and head writer Steve O'Donnell, it was a particularly cold betrayal.
48. Crispin Glover Pushed Him Too Far
If you're going to dish it out, you've got to be able to take it in return. On one of the most infamous episodes of Late Night ever, Crispin Glover appeared in-character while promoting a movie. Anyone who's seen Back to the Future knows Crispin Glover's a bit of a weird guy, and Letterman was clearly unprepared for his bizarre antics. Eventually, Glover kicked within inches of Letterman's face, and the host had had enough.
Letterman just walked off the set of his own show right then and there. Safe to say, it wasn't his finest moment—but it got a whole lot worse than that.
49. He Nearly Suffocated Richard Simmons
Maybe one of Letterman's most infamous feuds was with fitness guru Richard Simmons. Simmons appeared on Late Night and Late Show all the time, and the pair seemed to have a pretty close relationship—but that all crashed and burned after an appearance in 2000. Simmons was dressed as a turkey (just roll with it) and Letterman sprayed him in the face with a fire extinguisher (just roll with it). Unfortunately, the results were disastrous.
Simmons suffers from severe asthma, and the blast from the fire extinguisher resulted in a brutal asthma attack. Letterman made light of the incident, and Simmons was furious. He didn't come back on the show for over six years afterward.
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