The Final Letterman Appearance (2015)
After Letterman announced his retirement, Stern fretted about his final appearance on the Late Show for weeks. But the appearance was a huge hit, full of greatest hits from past appearances; Stern called out Paul Shaffer of being "baked" and accused Letterman of having checked out years ago. Stern had no idea Letterman would keep him on the couch for the night's second guest Don Rickles' final appearance on the Late Show. The result was a Mount Rushmore of comedy, with Stern appearing humbled next to one of his biggest comedy heroes. Rickles skewered Stern's "trick-or-treat hairdo" before praising him: "You are young, bright, terrific and I swear you are dynamite for the people. God bless you." Letterman looked confused. "What the hell was that? Good God."
As Stern predicted, Letterman's retirement didn't
last long. And the two aren't done teaming up; Stern just taped a long interview for
Letterman's Netflix series My Next Guest
Needs No Introduction.