It’s not easy to get Cher on your show. Just ask David Letterman, who asked her to appear on his late night talk show as a guest for four years and, by Cher’s account paid a $28,000 hotel bill to seal the deal. The reason she kept turning the appearance down? She thought he was an asshole. She didn’t just think it, she said it right to his face during her debut appearance on The Late Show with David Letterman on May 22, 1986.

While Letterman was probably aware of his reputation as a tough interviewer whose segments could go rogue, he was clearly not accustomed to his guests pointing it out to him — and certainly not on the air.

Cher's appearance got off to an inauspicious start. Her first conversation wasn't with the host, but bandleader Paul Shaffer, with whom she'd worked in the past. After successfully wrangling his guest's attention, Letterman tried some light-hearted talk, mentioning to Cher how much her liked her perfume. After revealing that she actually combined fragrances - and sensing how boring this line of discussion was for viewers - Cher looked at Letterman and smugly asked, "Is this as good as it gets?"

The conversation continued to be awkward yet cordial, until Letterman addressed the elephant in the room and asked the singer why she turned his show down for so many years. Being Cher, she just came out and said it: “I thought I would never want to do this show with you,” the star began, only to be immediately interrupted by Letterman, "Why, because you thought I was...," the host asked. "An asshole,” Cher responded.

Naturally, the audience immediately reacted - first gasping, then clapping, then booing.

“For you folks at home who may have missed that, she said she thought I was an awfully nice guy,” Letterman joked, pulling a face.

Cher went on to explain that she didn't have anything in particular against Letterman  — in fact, she was a fan of his show. But she’d seen things get “frightening” when the host spoke to guests he didn't like.

Watch Cher's 1986 appearance on 'The Late Show with David Letterman'

Almost no one could throw Letterman off his game, but - after briefly steering the conversation into friendly banter about Cher's tattoos - the host admitted, “You know, with that asshole remark, you kinda threw me off.”

“You’re the first person to call me that in person though,” Letterman continued. “I’m sure they mutter that on the way out sometimes,” the host joked, much to the delight of his guest.

Despite moments of awkwardness, both parties seemed to genuinely enjoy their chat. Letterman, who at various points stumbled through his questions, even revealed that Cher was one of the original guests he wanted to book when the late night show launched in 1982.

Within the conversation, Cher also brought up her "huge hotel bill," insinuating that someone on the show agreed to pay it in exchange for her appearance. "If you think this show will cover that hotel bill, you were sadly misled," Letterman responded - but was he being truthful?

In 2017, Cher brought up the now infamous charge during a concert at MGM National Harbor in Maryland.

“I had a $28,000 hotel bill and Dave Letterman had always asked me to be on his show,” she told the audience, as recounted by People. “And I said, ‘Yes if you have $28,000.’ But they said no.” Moments later, Cher got the answer she'd hoped for. “Then they called back and said yes!"

The award-winning singer and actress eventually made a handful of appearances on Letterman, including a memorable reunion with her former husband and singing partner, Sonny Bono, in 1987.

Decades later, as Letterman was bringing his late night run to a close, Cher made a surprise appearance. “For a number of years, there’s something that I’ve always wanted to get straight between us,” Cher explained during the 2015 appearance. “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.”

Before Letterman got too weepy, she added: “And you’re still an asshole.”

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