David Letterman‘s history as a late-night talk show host has been an impressive one. Letterman served as host of NBC’s Late Night with David Letterman from 1982 to 1993, then the host of CBS’ Late Show with David Letterman from 1993 to 2015, and is now the host of Netflix’s My Next Guest Needs No Introduction with David Letterman. Letterman’s name is synonymous with celebrity status. He’s gotten a chance to speak with all the big names across the industry, and his fame has risen to astonishing heights as a result.
However, along the way, there have been missteps. In fact, as far back as 1988, Letterman was making waves with Steel Magnolias star Shirley MacLaine calling him a “jerk” for how he treated her on his show. He’s also famously apologized for inappropriate comments he made about Monica Lewinsky during Bill Clinton’s sexual misconduct scandal.
Appearing night after night with the tightrope walk of being funny while avoiding crossing the line can’t be easy, but Letterman has made guests visibly uncomfortable multiple times. Here are some of the most notable.
1. Jennifer Aniston’s weird interaction with David Letterman
Back in 1998, Jennifer Aniston was at the height of Friends fame. Her appearance on David Letterman’s show included confessing that he intimidated her. “I love you, but I fear you,” Hello Giggles reports Aniston saying before things got weird.
Aniston talked about the weirdness of being a celebrity and getting recognized at the spa. They moved on to Aniston’s fear of flying, where he suggested Bloody Marys as the solution to her anxiety. Then he leaned close and said, “I’m sorry if this is rude,” as he put his face by Aniston’s hair. She shrieked and asked what he was doing, but he didn’t answer. Instead, he kept getting closer until he had taken a piece of Aniston’s hair in his mouth and sucked on it. Then he returned his chair to its position and handed her a tissue to wipe off her slobbery hair.
2. Jennifer Lopez and a leering camera
Another old clip surfaced of David Letterman being creepy toward Jennifer Lopez, who was there to promote her work on The Wedding Planner. At the very start of the interview, the camera crew did a close-up on Lopez’s chest. She gasped and then wagged her finger disappointedly in the camera’s direction while Letterman said, “That’s pretty good. It’s pretty good.”
Later in the same interview, he showed a photo shoot Lopez did for Rolling Stone and commented on how the bikini top she was wearing was “not necessarily your size.”
3. Madonna dodged peer pressure from Letterman
Madonna appeared on David Letterman’s show back in 1994. The Queen of Pop definitely had a reputation for flashy antics, but that didn’t make it any less creepy when Letterman tried to pressure her to kiss a stranger in the audience as soon as she got on stage. Madonna quipped, “Why are you so obsessed with my sex life?” but Letterman didn’t take the hint. He continued to pressure the star into the act before she curtly told him, “I’ve never succumbed to peer pressure.” The interview has since been held up on Twitter as an example of Madonna calling out sexism in the late-night TV world long before the mainstream did.
4. Janet Jackson after her Super Bowl halftime show
Janet Jackson’s infamous wardrobe mishap at the Super Bowl dominated tabloid covers and became the talk of her career for months. When she appeared on David Letterman’s show, she made it abundantly clear that she did not want to “relive” a moment that was painful for her. However, the talk show host didn’t back off and kept using the moment to crack more jokes.
5. Jessica Alba’s appearance on David Letterman
To promote Honey, Jessica Alba appeared on David Letterman’s show and opened up about feeling vulnerable in shots that required her to be dressed as an exotic dancer. She said it was “really, really hard” because she felt nervous about being so exposed. It’s clear from the context that Alba is trying to set boundaries around her comfort levels, but Letterman used the moment as a chance to sexualize her and quipped, “How tiny was it?” and “Where was it tiny?” as Alba asks him to stop.