Paris Hilton: 'How'd you like being in jail?'
When Paris Hilton appeared on Letterman's show in 2007 she wanted to promote her new fragrance but Letterman had other ideas, asking her almost immediately, "How'd you like being in jail?" An embarrassed Hilton looked out at the roaring audience before replying, "Not too much." Hilton later told Letterman she had moved on with her life and didn't want to talk about being in jail anymore, to which he replied: "That's where you and I are different. That's all I want to talk about."
Joaquin Phoenix: 'I'm sorry you couldn't be here tonight'
US actor Joaquin Phoenix appeared on Letterman in 2009 sporting a long beard and dark sunglasses. In the bizarre interview, the "Walk the Line" actor appeared distracted and uncomfortable, answering questions in a quiet voice and frequently scratching his beard. The interview turned out to be part of a bigger hoax that saw Phoenix convince fans he had quit acting to become a hip-hop star. Phoenix later said Letterman had not been in on the joke.
Justin Bieber: 'Canadian high school'
In 2012, baby-faced pop star Justin Bieber appeared on the show following the release of his album, "Believe." Early in the interview, Letterman asked Bieber about a new tattoo on his arm and warned him against getting more tattoos. "More and more you see the mural...the Sistine Chapel," Letterman said, motioning over his chest and shoulders. "I'm not going for the sixteenth chapel," Bieber replied, to laughs form the audience, leading Letterman to quip: "Canadian high school!"
Drew Barrymore: 'I can't thank you enough for that'
In her infamous appearance on Letterman's show in 1995, Hollywood actor Drew Barrymore told Letterman about a dance she had performed at club called "Blue Angel," and offered to do a demonstration for the host. Barrymore then climbed onto Letterman's desk and pulled up her top before kneeling down and kissing him. A clearly stunned Letterman told the actor afterward, "I can't thank you enough for that."
Letterman's confession: 'My response to that [allegation] is, 'Yes I have'.'
In 2009, Letterman told audience members that someone had attempted to blackmail him over incriminating information about his personal life. He told how he had received a package three weeks ago with a demand he pay $2 million. Letterman said a man had been arrested over the threats but used the opportunity to confess to having sexual relationships with women on his show.
Farrah Fawcett: 'That's what I had just asked you'
Farrah Fawcett's 1997 interview with Letterman sparked rumours that she was drunk or on drugs because of her rambling responses and bizarre behaviour.
Madonna: 'Why don't you go and kiss the guy in the audience?'
Tension was high in one of Madonna’s early interviews with Letterman who introduced her as one of the biggest stars in the world who had "slept with some of the biggest names in the entertainment industry". The pop icon told Letterman she was "only there because there wasn’t a [New York] Knicks game" and asked him, "Why are you so obsessed with my sex life?"
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