Seven awkward late night interviews: From Joaquin Phoenix to Madonna

From provocateurs to pranksters to, simply, a celebrity having a bad day

The late night interview is a tough gig, undoubtedly. Hosts like Conan O'Brien, David Letterman, and Stephen Colbert have spoken to countless celebrities in their time, but there's no guarantee the conversation will go smoothly.

From provocateurs to pranksters to, simply, a celebrity having a bad day or a line of questioning that ends up ruffling feathers – what makes for a terrible interview, however, can sometimes make for gripping television.

Here are some of the most brilliantly disastrous interviews ever to have aired on late night television.

Abel Ferrera on Late Night

Conan O'Brien has said his worst interviewee ever, in 25 years as a late night host, was director Abel Ferrera. The host told Dax Shepard on his podcast that Ferrera, best known for his films Bad Lieutenant and Dangerous Game, fled the set of his show before the interview was set to begin, running out of NBC’s New York headquarters. The show’s staff had to drag him back in.

“He came on camera against his will,” O’Brien said of Ferrera’s 1996 appearance. “And then came out, and I think he started yelling at me.”

Joaquin Phoenix on Letterman

With hindsight, we now know Joaquin Phoenix was deep in character when he appeared on The Late Show with David Letterman back in 2010, as part of his subversive mockumentary I'm Still Here. It's also since been confirmed that Letterman was in on the joke, after writer Bill Scheft told The Hollywood Reporter: "Dave knew about it and Dave loved it because he could play along. It was great television."

However, hoax or not, the interview still makes for a nail-biting watch, especially when Letterman ends with the line: 'Joaquin, I'm sorry you couldn't be here tonight."

Madonna on Letterman

The musician is a master at brewing controversy and her 1994 interview with Letterman is no different. Madonna begins by handing the host a pair of her underwear, which she later asks him to smell, before proceeding to say the word "f***" 14 times over the course of the 20-minute interview.

At one point she even brands Letterman "a sick f***", before making a series of sexual innuendos and criticising Letterman's style, adding that "money has made you soft."

Casey Affleck on The Late Show

It's an interview that's tense from the moment Affleck sits down, after Colbert makes a quick joke about the actor's casual outfit, to which he retorts in annoyance: "You're implying I'm being rude." Colbert then adds to the jab, calling him a "street corner Jesus". It's not long before a physical fight between the two is suggested.

Norman Mailer and Gore Vidal on The Dick Cavett Show

A 1971 episode of The Dick Cavett Show, during its brief slot on ABC's late night lineup, saw two literary heavyweights engage in a bristling face off. Writers Gore Vidal and Norman Mailer descend into a blazing argument when Mailer begins to attack Vidal over his essay for The New York Review of Books, in which he lambasted Mailer's view of women's lib and compared him to cult leader and violent misogynist Charles Manson.

Crispin Glover on Letterman

Though Letterman may have been in on Phoenix's TV prank, he had no idea that actor Crispin Glover had turned up to his 1987 appearance in character as "Rubin", from the then-unreleased film Rubin and Ed, complete with platform heels and a terrible wig.

After muttering that he "knew that this was gonna happen" and "the press, they can do things, they can twist things around", Glover then challenges Letterman to an arm-wrestling match, before delivering a karate kick that barely misses the host's head. Letterman simply walks off stage and the show cuts to commercial.

The actor had appeared on Letterman's show in 1988 to discuss her new film Madame Sousatzka, but became quickly agitated when the host kept probing her about her interest in past lives, which she had already written about in two books.

"Maybe Cher was right, maybe you are an asshole," MacLaine says, in reference to a previous interview in which Cher had confessed she was hesitant about being interviewed by Letterman.