The 12 Craziest Moments From The Late Show With David Letterman
We here at Top Socialite got a huge kick out of David Letterman demolishing Paris Hilton on Friday night, and so we started remembering all of the great moments from The Late Show and decided to make a list of our favorites. We couldn’t find every moment we wanted on YouTube (no watermelons being dropped unfortunately), but we think this is a pretty fair list of the craziest moments from the show.
12. Sandra Bernhard:
Check out the 1988 presidential debate discussion about 2:05 in, where Sandra Bernhard asks Dave who he’s voting for, and he drops Ron Paul’s name!
11. Dave Wears A Suit Made Of Alka-Seltzer:
One thing Letterman has always been willing to do is some goofy tricks and stunts, and this is one of his greatest of all time.
10. Fruit Basket for General Electric:
Dave goes to meet his new employer and gets a rude reception. Make sure you stick around until the end for the special G.E. handshake.
9. Borat:
“Why are we laughing?” “I’m not sure.”
8. Dave gets terrified by a visiting rhesus monkey:
I’m not sure which is stranger, the monkeys or the woman tending them, but hilarity definitely ensues.
7. Pee Wee Herman:
Pee Wee Herman made several awesome appearances back in the 80’s and it was hard to choose just one, but he was a Halloween tradition there for awhile.
6. Harvey Pekar:
This interview is portrayed in American Splendor, the movie about Harvey Pekar’s life.
5. Cher:
Cher gives a great and lively interview here, calling Dave an asshole about 3:30 into the first clip. Both halves of the interview are definitely worth watching as this is as great a display of Dave’s interviewing skills as I’ve ever seen.
4. Sam Kinison:
Sam Kinison’s appearance on David Letterman was his first in front of a national audience, and the energy coming off of the guy is absolutely incredible.
3. Crispin Glover:
I am not sure if this was an act, or if Crispin Glover is really this big of a freak, but it’s really strange to see Marty McFly’s old man acting like this.
2: Drew Barrymore flashes Dave:
Quick clip and to the point, but easily one of the most famous clips in the history of the show. And wow, I had forgotten that Drew Barrymore was pretty hot back in the day.
1. Andy Kaufman Gets Slapped and Flips Out:
Another David Letterman moment that appeared in a feature film, Andy Kaufman gets into it with Jerry Lawler with pretty hilarious results.
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18 Responses to “The 12 Craziest Moments From The Late Show With David Letterman”





What about the entire show devoted to Warren Zevon…..I would think that would be in this list.
How bout the Madonna multiple F-bomb interview
I was always a big fan of Dave when he did that consumer advocate show “Fight Back with David Letterman”
If you put up the Alka Seltzer suit, you have to put up the velcro suit. That was just as hilarious.
My personal favorite was when Dave had (I believe) Robin Williams on as a guest. At the time, Dave would throw a pencil through the (fake) window behind him, and they would play a glass-breaking sound. Well, Dave would do it, get the sound, then Robin would, and nothing would happen. A couple more rounds, and the same result (I think the sound guys were having a joke at Dave and Robin’s expense).
After a quick cut to commercial, and when the show came back, the frames of the windows were covered with pencils stuck into the wood. I have no idea where they got all the pencils that quickly (yes, I know it was prerecorded), but I thought it was hilarious.
Good call Nate.
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No Richard Simmons?
[…] Top Socialite has created a youtube link-up with 12 of the craziest moments on the David Letterman show. My personal favorite is the one playing below where Letterman put on a suit with thousands of […]
technically not Dave, but Chris Elliot, or ‘The Man Beneath The Stairs’ drinking a bottle of Wesson oil was ingrained on my mind from the moment it aired. May have been the peak of Elliot’s career.
er, seats i thk, not stairs.
Crispin Glover was just doing his character from Rubin and Ed. Same pants, same shoes, same weird.
I think my fave moment was when Letterman told Poppa Bear that he (Dave) felt that (paraphrasing) “85% of what you say is crap.” The rest of the bit was Dave laying into O’Reilly and while maintaining *most* of his composure, he was showing that he was really cheesed, which was sorta refreshing, in a way.
It’s telling that a disproportionate number of these clips are from the first several seasons.
[…] The 12 Craziest Moments From The Late Show With David Letterman […]
My favorite is the one with Chris Farley and he made the ‘best entrance to the dave letterman show ever’ -David Letterman
Yea dave definitely got alot softer when he moved to cbs. The first couple of years weren’t that bad, but now he’s a wuss. He even admitted so in an interview after the madonna thing, that in his earlier years he wouldn’t have been so nice to her.
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