The Dark Truths About The David Letterman Show

1. David Letterman admits to having s*x with staffers

Image Source: Vanity Fair

Letterman took to his own show to admit to the fact that he slept with a lot of his female staff. While the extortion (below) that followed was also made public, the full nature of what happened was not. Was it consensual? It's always hard to say when there's a power dynamic such as this one.

2. He was part of a $2M extortion plot

Image Source: Reddit

Back in 2009, David Letterman admitted that he had to testify before a grand jury for an extortion plot against him. He received a package containing a threat to be exposed for his indiscretions unless he paid up, so Letterman gave the blackmailer a phony check for $2M.

3. Many feel the scandal is should be re-evaluated

Image Source: Reddit

When Letterman made these confessions, honestly, the world kind of met them with a shrug. Some people feel that these cases should be re-explored in this post-#MeToo movement era. Power dynamics and consent are much more part of the conversation now than they were then.

4. Mind you, he was married while this was happening

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To add insult to injury, Letterman was not a single pringle when these allegations started hitting the news. In fact, he had a long time partner and a kid when the rumors started swirling. He tried to frame his silence as him protecting the women and his own family, but either way, this was not a good situation for anyone involved!

5. He's been the center of extortion before

Image Source: Wikimapia

A few years before the scandalous events, David Letterman found himself the target of an extortion plan. His handyman at his massive ranch was arrested and charged with trying to kidnap Letterman's SON in exchange for a large sum of money. The handyman pleaded not guilty, but served 10 years in prison.

6. Letterman is quick to point the finger

Image Source: The Hollywood Reporter

When David Letterman's indiscretions became public, he took to his show to quickly point out the indiscretions of others. He spoke about the infidelities of others as if trying to lessen his own. Of course, as a late night host, the jokes were sure to abound, but something can be said for the lack of accountability.

7. His love life is a mess

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It makes sense that after these allegations came out, it jeopardized Letterman's own marriage. He apologized on air in 2009, saying that he had been unfaithful and that his wife was very hurt by his actions (duh!). It was again discussed in 2013, saying at that time he was still trying to make up for it.

8. He allowed a lot of inappropriate moments on his show

Image Source: Radar Online

As the host of a late night show, there's a fine line between being a bit wild and fun and keeping the show network appropriate. Way back in 1995, Drew Barrymore was a guest on the show, and in honor of Letterman's birthday, she began to gyrate on his desk and then proceeded to flash him. Of course, Drew was also in a different place in her life at this time, but it goes to show what David allowed on the show.

9. Madonna gave David her underpants

Image Source: Rolling Stone

Another infamous moment that happened on The Late Show is when Madonna dropped the F bomb multiple times when appearing on the show. It became the most censored episode of television in talk-show history. Madonna also made a weird comment about giving Letterman her underpants.

10. He had a pretty serious stalker

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Back in 1998, a woman named Margaret Mary Ray who was suffering from mental illness began stalking Letterman. She believed that the two were in a relationship and proceeded to steal his car and enter his home. She unfortunately committed suicide later that same year.

11. Once a cheater, always a cheater?

Image Source: Radar Online

Letterman had a long-term girlfriend who was also a writer named Merrill Markoe. A lot of people credit her for his success, as she created some of his most popular segments. Merrill wrote about her relationship with David in her memoir and saying that he told her that he would never cheat on her.

12. He doesn't respect women's boundaries... not even Janet Jackson!

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For those of you who have forgotten, Janet Jackson performed at the Super Bowl with Justin Timberlake and had an accidental nip slip. Live, in front of millions. Talk about mortifying. As if that wasn't enough, when she went on Letterman, she asked him repeatedly to stop talking about it, and he kept pressuring her to relive the moment. Rude!

13. Employees have said it's a hostile work environment

Image Source: Salon

There have been several reports from former staffers who have agreed that while David is talented, the workplace is not ideal. Many have cited unfair work practices, being severely underpaid, and feeling awkward around the TV show host. Most women have stated that Letterman at least made a pass or gave them extra attention even if he was not inappropriate.

14. He groomed his staff members

Image Source: Salon.com

Regardless of gender, David Letterman was known to groom his staff members in order to get what he wanted. He started small with typical requests of picking up lunch, but he wouldn't tell interns his preference and the reprimand them for it. Then he'd increase to asking people to pick things up for him at his hotel room. All of this was setting the stage for an abuse of power.

15. David's famous feud with Jay Leno

Image Source: Esquire

David Letterman and Jay Leno had a feud that lasted for years after Leno was named the host of The Tonight Show over Letterman. Conan O'Brein was also involved when Letterman told him that Jay was a brat. Jay took the high road and never responded to the comment publicly.

16. He pushed Lindsay Lohan to talk about her rehab

Image Source: The Independent

Once again, this man cannot respect boundaries, whether sexual or otherwise. When Lindsay Lohan was a guest on his show, he repeatedly pushed her to talk about her rehab when she clearly didn't want to. Isn't it his job to make his guests feel welcomed? Of course, as a comedian, he can push the envelope a bit, but there still needs to be a respect of boundaries!

17. He almost died in 2000 because of his heart

Image Source: New York Daily News

In 2000, David Letterman had to have sudden quintuple bypass surgery, because his heart was so bad. He often joked on the show about his high cholesterol. He had to take a five week break from the show to recover, and his return gave the show ratings a significant boost.

18. He made Jessica Alba visibly uncomfortable

Image Source: IMDb

This man is known for his inappropriate and awkward interviews at this point! Once when interviewing Jessica Alba, she was talking about an outfit she had to wear for the film Honey

. He proceeded to pressure her to describe the outfit... how tiny it was, where it was tiny, and she even said he was making her nervous, but he still pushed.

19. He shamed the female staff into keeping quiet

Image Source: The Mirror

It's been reported that while the relationships David was having weren't necessarily a secret, people involved felt that they had to keep it quiet because they were ashamed. Reports have said that he would openly look people up and down and do degrading tasks around the office.

20. One of the women he slept with was an intern

Image Source: Radar Online

What's now known as Interngate is a prime example of those power dynamics. After it came out that Letterman was having s*x with staffers, Holly Hester came forward saying she had a year-long affair with him while she was an intern. She said that things ended due to their age difference, but it came out that he had a secret apartment to bring young girls.

21. Before his feud with Jay, he helped him revive his career

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When Letterman was a successful host on "Late Night" in the 80s, Jay Leno's career seemed to be bottoming out. In order to help him out, Letterman brought Leno on as a guest, which gave his career a boost as the show was very successful. They had a great chemistry that revived Leno's career.

22. He's ogled women who were his guests

Image Source: DailyMotion

Again, this comes down to the environment that Letterman as the host of the show is creating. When Jennifer Lopez came on the show to promote her film, The Wedding Planner

, one of the cameramen zoomed in on her breasts, and stayed there, much to the amusement of David.

23. He had a secret bedroom at his TV studio

Image Source: Reddit

Yuck. It's been reported that David Letterman kept a secret bedroom at the studio for his "favorite women." Only a few select female staffers were allowed in the restricted area. His staff members refer to it as "the bunker." Truly, how is this man still on television?

24. He implied that Beyonce likes it rough

Image Source: Beyonce Online

When Beyonce made a guest appearance on his show, she mentioned how she often gets bruises during rehearsal, because she's so in it. David Letterman took this as an opportunity to make a crude comment, implying that Beyonce must also like rough s*x. Boundaries, my dude!

25. He was hooking up with as many people as possible

Image Source: Salon

It wasn't like David Letterman just had an affair once. Staffers report that he was hooking up with interns, with pages, with colleagues. Basically anyone and everyone who would go to bed with him, he was down. It didn't matter if they were a guest on the show or his assistant, he treated his job like a hookup app.

26. He's considered the worst Oscars host of all time

Image Source: The Hollywood Reporter

Okay, so this didn't happen on his show, but many consider his hosting of the Oscars to be perhaps the worst in history. He's known for his humor and his talk-show hosting abilities, of course. But his time on the Academy Awards was more awkward than anything else. He later joked about it saying he didn't realize that what he was doing would be televised.

27. Not even Oprah was safe

Image Source: NZ Herald

Honestly, as a woman of color, this situation speaks volumes. While he didn't hit on her like some of his other guests, he chose to question her intelligence instead. When an audience member heckled Oprah for her choice to speak out on important issues, instead of defending her, Letterman chose to mock her and what she was saying. Insert eye roll emoji here.

28. He paid his staff out of his own pocket

Image Source: The Wrap

It's to be said that while his actions were gross, David Letterman did try to take care of his staff. When the writers went on strike, he chose to ensure that the rest of the staff was paid throughout the time. Sources say that this money truly did come out of his own pocket to ensure everyone was taken care of.

29. He once put Jennifer Aniston's HAIR IN HIS MOUTH

Image Source: Reddit

Seriously! No means no, David Letterman. When he was interviewing Jennifer Aniston, he stopped the interview to put her hair in his mouth. Yes, you read that right. She was clearly uncomfortable and asked what he was doing. He, of course, did this without her consent in front of an audience.

30. His career after Late Show took a serious turn

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As if to make up for the horrific interviews he's given over the years, he's taken a more serious turn in his career. With his show "My Next Guest Needs No Introduction," it's apparent that Letterman is trying to take a more earnest approach with his interviewees, redeeming himself by showing genuine curiosity and interest.