It takes two to tango, and in this case, it took two celebrities to make television viewers deeply uncomfortable. When Madonna stopped by the David Letterman show in 1994, things quickly got weird. First, David began pressuring her to kiss a random person in the audience, refusing to take no for an answer.
Then, Madonna made everyone cringe when she revealed she had given David a pair of her undergarments, telling him to show the audience. The interview was so uncomfortable and inappropriate we couldn’t turn it off fast enough! Let’s be fair, put these two in a room together and things are always going to get awkward.
Jeff Goldblum, talking to Cavett in 1992, had starred in “Invasion of the Body Snatchers,” “The Big Chill,” and “The Fly,” long before he would lead the "Jurassic Park" franchise. It's safe to say that he was already a huge name, and things were only going to get bigger for him after this interview.
Goldblum was caught off guard in this interview when Cavett informed him that writers often describe him as “gangly.” Cavett attempted to soften the question by describing the time a man ridiculed him for his short stature, but the conversation was slow to start after that “gangly” remark.
Taylor Swift’s dating history is almost as newsworthy as her music career. Like most of us, however, she would rather not talk about her famous exes. Unfortunately, Ellen DeGeneres didn’t give her a choice. And it's kind of unavoidable, as Taylor Swift's celebrity dating history is kind of incredible.
During their interview, Ellen projected images of Taylor’s exes on a massive screen, basically implying that she had dated many men. Though a visibly-uncomfortable Taylor told the host that she doesn’t know if she's going to rehash her past relationships, Ellen said, “Yeah, you will.” Ellen got her way eventually. Talk about awkward!
While it’s quite common for talk show hosts to tease answers out of their celebrity guests, it’s often done in a tasteful and humorous way. Sadly, that wasn’t the case when singer Mariah Carey visited the Ellen DeGeneres show in 2008. She was about to be forced to reveal some pretty private news!
The host demanded that Mariah address the rumors of her pregnancy, even pressuring her to drink an alcoholic beverage to prove that she wasn’t pregnant! Naturally, the mom-to-be was forced to admit her very private news, later calling the event “extremely uncomfortable.” Not cool at all, Ellen!
There are some moments that most people would prefer to forget. Moments like going to jail, for example. Unfortunately for celebrity Paris Hilton, David Letterman wasn’t going to let her off that easily. Though their interview began pretty casually (talking about different cities), David began asking the socialite about her 2007 stint in jail.
A visibly uncomfortable Paris initially answered David’s relentless questioning before telling him she would prefer not to talk about it since she’s moved on — a hint she hoped the host would take. We can't keep up with how many times this kind of thing has happened on Letterman's show over the years.