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.
Norman Mailer & Gore Vidal
Dick Cavett couldn’t help noticing Norman Mailer and Gore Vidal were engaged in a tit-for-tat feud played out in print media. So, he invited two towering intellectuals to face each other on his show in 1971.
It was vicious. At one point, Mailer accused Vidal and the rest of the panel of being intellectually inferior to himself. It was then that Cavett suggested that Vidal might like two other chairs to contain his giant intellect. By the end, the entire audience vociferously turned against Mailer. Cavett made some enemies during his tenure, but that's expected for any late-night chat show host.
Arnold Schwarzenegger
Bill Clinton surprised everyone as the first sitting president to make a late show appearance. By 2003, Arnold Schwarzenegger would take politics and celebrity to a new level when he went on "The Tonight Show" with Jay Leno to announce his run for governor of California.
He told Leno that he supports the recall of the current governor, and then he announced his plan to unseat him. As would be expected, yet shocking at the time, Schwarzenegger went full Terminator on the California governor. Let's face it, has there ever been a late-night chat show interview involving "The Governator" that wasn't hilarious?
Taylor Swift
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!
Madonna
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.