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.