Most lists were group efforts, executed quickly, per O’Donnell. “Sometimes we’d write 100 of them. Then I’d pitch the best to Letterman minutes before the show. He’d pick a couple, add a couple.” The ...

Millie is a writer and content creator working in media and entertainment since 2012. Her work has been recognized by esteemed publications such as The New Yorker, Buzzfeed News, The Washington Post, ...

Late Night host David Letterman had already put on a suit covered in Alka-Seltzers and lowered himself into a vat of water. Really, how do you top that? On September 18, 1985, he debuted a future ...