He was a former weatherman and a failed morning-show host who perfected a sort of snide, irreverent attitude towards showbiz types. After getting noticed by Johnny Carson and making a fan out of NBC bigwig Fred Silverman, however, David Letterman found himself taking his goofy antics to a 12:30am time slot — and thus, a late-night TV legend was born. When Letterman announced during the taping of his show today that he would definitely be retiring next year, he signalled the beginning of the end of a three-decade-plus career of entertaining people in the wee small hours. And while he was definitely the reigning King of Late-Night Smart-Assery, Letterman could also do wonders with a celebrity interview —the stranger or more shocking, the better.
In honor of The Late Show‘s host saying he was rounding the track for his last lap, we remember six of his most iconic interviews. From nearly taking a kick to enduring performance-art schtick, here’s a six-pack of Dave behind the desk, on his toes and at his best.