According to IMDB, Howard Stern has been on “David Letterman” 23 times, five of them during his 11-year stint on NBC and 18 on CBS's “Late Show.” The radio legend is set to make it 24 during tonight's episode, and sadly — unless Letterman decides to come out of retirement and flash his famous grin at us from some other platform — it will also be his last.
Speaking of, check out this excellent montage by Youtuber Sean Bradley that highlights Howard's 30-plus year history with the king of late-night, from his very first appearance in June 1984 to today. His self-promotional genius and willingness to do anything for a punchline make him one of the great recurring guests, and the only one, as far as I know, who never shied away from bashing Jay Leno on the air.