30 most shocking late night scandals

11. David Letterman and Oprah Winfrey have a years long feud

It’s not unusual to have seen Oprah Winfrey as the butt of the joke on many different television shows. Late night TV show and sketch comedies alike would often turn to her for fodder. Perhaps she’s easy to make fun of, but it seemed nobody enjoyed attacking her more than David Letterman on his show.

For years, Letterman would take constant pot shots at Oprah on his show. He wouldn’t specifically say why he didn’t like her. He just would take very opportunity to joke about her negatively. Letterman would also sarcastically plead for her to come on the show as a guest. But nobody could really seem to figure out what spawned this feud.

Eventually Oprah came on Letterman’s show in 2005, in a start to smoothing over the tensions. Ten years later, Oprah herself would finally address what started their tiff. According to her, it dates back to her 1989 appearance on the show. She says the experience was miserable for her, with David “baiting the audience” at her expense. But for what it’s worth, the two were able to bury the hatchet after Letterman politely kissed her hand and apologized.