Grudge Match: David Letterman vs. Conan O'Brien


When I heard last week that NBC was going to replace Conan O’Brien with Jimmy Fallon, my first response was: Jimmy Fallon?
Because, like, I assumed they would want someone funny in that time slot. But, like, Jimmy Fallon is decidedly NOT funny.
Anyway, the reason they’re replacing Conan is because Conan is replacing Jay Leno, who was once thought to be funny at 11:30 but now apparently is not funny or not hip or not something enough for 11:30 and will instead go back on the road full-time as a (very rich) standup guy.
Through it all, though, David Letterman has been rock steady. Yeah, he’s switched networks, and, yeah, he switched time slots. But this guy’s been a staple of late night TV since 1982.
My Grudge Match foe, Danny – who was probably in diapers when Letterman first came to late night – thinks Conan O’Brien is funnier than Letterman. But, of course, he’s wrong, as most Scots are. Not only is Letterman funnier, but there wouldn’t be a Conan without a Letterman since his style of comedy is completely taken from the Letterman book.
I could give you a thorough analysis of that, but instead, I’ll give you the Top Ten Reasons Why Letterman Rules Late Night and Always Will:
10. Johnny Carson loved him.
Johnny, of course, wanted Letterman to replace him when he left “The Tonight Show.” But for some reason NBC chose Leno, who had been a longtime guest host. Carson stood by Letterman, though, occasionally sending Letterman jokes, which Dave used in his monologues.
9. Letterman was from Indiana.
Sorry – can’t help feeling a little loyalty to my roots. But I spent 18 years in Indiana, and, in fact, my wife used to wait on Dave’s mom at this tea house she worked at in Indianapolis. Anyway, I think Dave’s Midwestern background provides a bit of the cynicism that fuels his humor. Whereas Conan is from -- Boston? Yuk.
8. The Top Ten lists are STILL funny. Even after 26 years, they’re still fresh.
7. Larry Bud Melman in a bear suit!
Dave had a knack for making ordinary people funny. And this was the case with Calvert DeForest, the grumpy, doughy sometimes correspondent.
6. Awkward moments with celebs. Madonna cussed him out. Cher called him an ---hole. Crispin Glover tried to kick him. And Shirley MacLaine? Not sure what that was all about. But it was great TV.
5. Dave’s reaction to getting flashed by Drew Barrymore.
Priceless.
4. Andy Kaufman.
The famous wrestler incident is still one of the greatest moments in comedy.
3. Dave harassed his bosses.
GE execs (who headed NBC after GE bought the network) were regularly ticked whenever Dave made fun of them, often calling them “pinheads.” Here Dave even tried to pay them a visit.
2. Rupert.
Dave’s bits with a deli owner across the street have always been hilarious. Here is one of my all-time favorites.
1. Dave at Taco Bell.
In one of my favorite moments from the show, Dave worked the drive-through window at a Taco Bell in New Jersey. Classic, classic Letterman.

Pat, Pat, Pat… Impressive as your links are, you lost me in the second sentence. Jimmy Fallon isn’t funny, indeed.
However, this isn’t a discussion about Jimmy Fallon, this is about Conan beating the laughter right out of Dave in a beat-down so one-sided I actually feel sorry for Letterman. Oh, and Pat, you’d better watch those insults to us Scots, or you’ll end up with a claymore where… Well, where you probably don’t want it.
Letterman has done one thing for the past 26 years. OK, he’s done a decent job of it, but you’d expect that after doing it for so long. Conan, on the other hand, has what I feel to be a far greater legacy to his name. He was a writer on SNL for three years, during which time he wrote “Mr. Short Term Memory” and “The Girl Watchers”, amongst other excellent skits. After that, he became a producer/writer on the Simpsons, that’s right Pat, Conan wrote on your favourite show of all time, yet you stab him in the back by suggesting that Letterman is better. He wrote Marge vs. the Monorail, one of the best episodes ever!
Let’s focus on some direct comparisons between the two for a second
- Letterman’s teeth look like they are the product of some evil genetic experiment splicing horse and human DNA together. Seriously, they are frightening. Conan’s teeth appear pretty normal.
- Conan’s hair is awesome. Letterman’s is… disappearing.
- Conan has Triumph the Insult Comic Dog and Max Weinberg. Letterman has Paul Shaffer. No contest.
- Letterman is perpetually near death, the guy had a quadruple bypass in 2000. Conan is fully functional.
- Conan is stalked by priests. Letterman has far more boring stalkers.
At the end of the day though, it comes down to this. Conan = funny, Letterman = tired, bitter old man who’s still mad at being passed over for the Tonight Show gig. And I, personally, can’t wait until Conan takes that position over.
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Exactly what the heck is a claymore?
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A claymore is a huge long sword. Pat, haven't you seen Braveheart?
Danjen, you've a good point with the skean dhu - you would even be able to have the element of surprise!
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Alba gu bra. (Quote from Braveheart)
A claidheamh mor (claymore or great sword) was a bit too big to insert into any part of the human anatomy as it was about 55 inches long. Smell Gibson must have been pretty stong to wield that offensive weapon (and also do a Shrek impersonation at the same time!) as it was a big, heavy bit of ironmongery.
Danny - I still think that a sneaky skean dhu - or a dirk would be far more effective.

danjen said,
Wed, 05/28/2008 - 10:33am -
Conan O'Brien has Irish ancestry so, as he may be a Celt, he can appreciate it when a skean dhu is used instead of a claymore... far less invasive - but just as deadly! Simpson's writer - well then .... no contest!!
Letterman -Big teeth scare me - I think of tombstones. hmmmn