| Hint | Guest |
|---|
| 1982 -This famous comedian was smacked off his chair by fellow guest and professional wrestler Jerry Lawler, in an incident that was later revealed to be staged. | |
| 1986 - After Dave asked this guest why she thought she would never do a show with him, she said that he was, to wit, 'an ***hole.' | |
| 1987 - Several appearances with this underground comic artist lead to him calling Dave a shill for General Electric and Dave calling him a 'dork.' | |
| 1987 - Letterman went off to 'check on the Top 10' after this character actor began kicking the area in front of Dave in gigantic platform shoes. | |
| 1994 - After a foul-mouthed tirade and several rounds of boos from the audience, this singer began to espouse the benefits of peeing in the shower. | |
| 1995 - Dressed in drag and promoting his book, 'Miss America,' Letterman called this comedian ''the single ugliest lifeform he'd seen.' | |
| 1995 - As a birthday present to the host, this actress performed a strip tease on his desk that ended with her flashing her breasts to Dave. | |
| 1997 - This '70s icon made several attempts to get through some anecdotes with some prodding from Letterman before mistakingly thinking the set's backdrop was a window. | |
| 1999 - After this indie director's somewhat addled and giggling appearance, an irritated Dave said 'this, by the way, is why they invented childproof caps.' | |
| 2004 - 'The Letterman Years' for this rocker began after she also flashed Dave on his desk and was arrested later that night at one of her shows for assault. | |
| 2005 - Years after a supposed feud between these two, this media mogul finally deigned to reappear on Dave's show. After he went on her show. | |
| 2006 - This fitness guru and frequent Letterman target's new Steam Heat vegetable steamer product appeared to catch fire after being turned on. | |
| 2007 - Promoting her new fragrance, Can Can, this heiress was shocked that the fourth question out of the gate from Letterman was, 'how'd you like being in jail?' | |
| 2008 - After this guest cancelled in order to focus on the economy, Dave showed a live feed of this senator preparing to be interviewed by Katie Couric. | |
| 2009 - His eccentric and combative appearance on Letterman's show later turned out to be a stunt that the host was not let in on for the movie 'I'm Still Here.' | |
Chat Acronyms (Common)
Seven Dirty Words
3 Letter Body Parts
