Letterman Meets Miss America (1995)
Stern's second book, Miss America, suffered no sophomore slump: It quickly shot to the top of the New York Times bestseller list and became the fastest-selling book of 1995. "Ladies and gentleman, we are very near the end of civilization," said David Letterman while ruminating on those facts. Stern celebrated by showing up to the Late Show in full drag. He accused a visibly uncomfortable Letterman of staring at his chest and ended up kissing the host on the lips – something he would try (and fail) to do again during his last appearance on Letterman 20 years later.