Cher finally agreed to do Letterman’s show—but only after calling him out on live TV: "Kinda threw me off.."
Getting Cher on a talk show is not an easy feat at all. David Letterman would agree with us after finally being able to get her onto his show after 4 years of persuasion, and according to Cher herself, he even paid a $28,000 hotel bill to convince her, People reported. The reason she kept saying no? She thought he was an “asshole.” She didn’t just think it, she told him to his face when she finally appeared on 'The Late Show with David Letterman' on May 22, 1986. Letterman was known for being a tough interviewer, but he wasn’t used to guests calling him out on-air.
Cher’s appearance started off awkwardly. Instead of talking to Letterman right away, she chatted with bandleader Paul Shaffer, whom she had worked with before. When Letterman finally got her attention, he tried to start with some light conversation, telling Cher he liked her perfume. She explained that she mixed different scents, but then, realizing the conversation was dull, she smirked at him and asked, “Is this as good as it gets?” Things remained tense but friendly until Letterman asked why she had turned him down for so long. Cher didn’t hold back, "I thought I would never want to do this show with you," she said.
Letterman quickly interrupted, “Why, because you thought I was…?” "An a--hole," Cher finished. The audience reacted with gasps, claps, and boos. Letterman tried to play it off, joking, “For you folks at home who may have missed that, she said she thought I was an awfully nice guy.” Cher clarified that she didn’t dislike him personally, she was actually a fan of his show, but she had seen how rough he could be on guests he didn’t like. Even Letterman, who was rarely thrown off, admitted, “You know, with that a--hole remark, you kinda threw me off.” He then joked, “You’re the first person to call me that in person though. I’m sure they mutter that on the way out sometimes.” The audience laughed, and Cher seemed to enjoy the moment too.
At one point, she mentioned her “huge hotel bill” and hinted that someone from the show agreed to cover it to get her on. Letterman shot back, “If you think this show will cover that hotel bill, you were sadly misled.” But was he telling the truth? In 2017, Cher brought up the story again during a concert. She told the crowd, “I had a $28,000 hotel bill and Dave Letterman had always asked me to be on his show. And I said, ‘Yes if you have $28,000.’ But they said no.” However, she then revealed, “Then they called back and said yes!" The Things reported. Cher ended up appearing on Letterman’s show several more times, including a memorable 1987 reunion with her ex-husband and singing partner, Sonny Bono.
Years later, as Letterman was nearing the end of his late-night career, Cher surprised him with a heartfelt farewell in 2015. "For a number of years, there’s something that I’ve always wanted to get straight between us," she said. "This is one thing that I really mean from the bottom of my heart, I’m not kidding, no bullshit: I really love you and I’m going to miss you.” But before things got too sentimental, she added, "And you’re still an asshole," Entertainment Weekly reported.