Cher once kissed David Letterman in a wild TV moment years after calling him an 'a—hole': "I would..."
When David Letterman’s late-night talk show ended, he had amassed great wealth and spent it in fascinating ways. However, his most significant achievement was the legacy he built, leading many celebrities to celebrate him. At times, though, Letterman upset his guests so much that they walked out. One of the most memorable instances involved Cher, who initially seemed to dislike him but later shared several on-air kisses with him. In the early years of Letterman’s career, he had a much sharper edge. In 1986, when 'Late Night with David Letterman' had been on air for only four years, Cher finally appeared on the show after repeatedly refusing invitations, as reported by UCR.
Before Cher walked onto the stage, Letterman emphasized how important it was to have her as a guest. Speaking to the camera, he explained, "We've wanted to have this woman on the show for four years. How many times did we ask her? How many separate communications have we launched from our office to her? At least 81. We've, we've asked her to be on the show 81 times and finally, apparently through a lapse of judgment. Anyway, she's here tonight. And, of course, I'm talking about Cher." Since Letterman was known for his sarcasm, some may have assumed he was exaggerating. However, when Cher entered the stage, she confirmed that he had indeed been trying to get her on the show for years. Her demeanor further suggested that Letterman’s claims were true, as she appeared distant and unimpressed. Early in the interview, she asked him, "Is this as good as it gets?" Things only got worse for Letterman from there.
Cher revealed that she had only agreed to appear because the show’s producers covered a costly hotel bill. When Letterman changed the subject, he asked why she had avoided his show for so long. Cher has always been known for her honesty, so when pressed for an answer, she did not hold back. "I thought that I would never want to do this show with you," she said. When Letterman asked her to elaborate, she bluntly told him that she thought he was an "a*****e." When the audience booed her response, Cher seemed amused rather than bothered. She even admitted that before the interview, she had complained about Letterman to his staff. Looking around the set, she tried to spot the person who had heard her remarks. Letterman, seemingly caught off guard, admitted that her words affected him. Though he was known for his humor, he repeatedly brought up her insult, suggesting that it had truly thrown him off. Eventually, the interview took a lighter turn. Cher even told him, "I think you're cute," Entertainment Weekly reported.
Throughout her career, Cher has achieved remarkable success across multiple fields, making her one of the longest-lasting entertainers in the industry. Because of her longevity, she and Letterman had numerous interviews, and over the years, their dynamic changed. The two frequently flirted, and there is even a twelve-minute montage on YouTube showing their playful exchanges over the years. Not only did Cher and Letterman flirt, but they also shared a few surprising kisses.
In one instance, after performing with her band on his show, Cher kissed him on the lips. In response, Letterman leaned in for a seemingly real kiss, catching her off guard. Cher pulled back and commented on his attempt to kiss her several times. Afterward, she gestured for him to "come on," but no second kiss followed, it was just casual fun and games for the both of them, surely not for the viewers though! Years later, as Letterman’s career as a talk show host was coming to an end, Cher appeared on his show to bid him farewell. She expressed how much she would miss him and then gave him a tender kiss on the lips.