Understanding the Most Misunderstood Man on Late Night TV

“David Letterman sucks.”

“David Letterman is nothing but a curmudgeon. He hasn’t been funny in years.”

“If David Letterman was a food, he would be a Brussels sprout, because he leaves a bad taste in your mouth and everyone hates him.”

These are the things I have heard about David Letterman over the years. It just so happens that in my circle of friends, I’m the only person who seems to disagree with the above statements. I’m in my 20s and although I’d rather not admit it, I’m part of what the marketing gurus call Generation Y. According to them, I walk around all day tweeting about everything I eat and I need to be reminded that I’m special no less than seventeen times a day.


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Well they’re wrong. I need to be told I’m special at least twenty times a day.

All kidding aside, it seems that Letterman’s humor is lost on most of the people in my generation and that’s really a shame. Everyone seems to gravitate toward Jimmy Fallon, a guy who works his ass off for laughs and has a talent for creating bits that go viral on the Internet. I have to admit, I laughed at the “Get to the Choppa” bit that he did with the Governator himself.

But in general, his jokes all seem to be gimmicky and dumbed-down to me. I imagine the writers of his show picturing their target audience as a bunch of people drooling all over themselves. I almost feel as if they’re insulting my intelligence by expecting me to laugh at a fucking lip-sync battle. Also, watching him dress up as a woman and do “The Evolution of Mom Dancing” with Michelle Obama makes me a little sad for his dignity. When I watch that skit I get the same feeling in my gut that I get when I see someone’s dog wearing a sweater. “You poor thing, they had to take your dignity too?”

The other thing I don’t like about Jimmy Fallon is his lousy interviewing skills. If I had a dollar for every time I’ve heard him ask a guest, “Why are you so awesome?” I would be drinking umbrella drinks on a beach in Fiji right now instead of writing this article.

On the upside though, at least Jimmy Fallon has some musical talent and seems like a genuinely nice guy. If he’s happy doing gimmicky jokes and people continue to watch him in droves, then good for him. He’s just not for me.

A lot of people my age seem to really like Jimmy Kimmel as well. Jimmy Kimmel seems to be just as focused on creating viral YouTube videos as Fallon but he’s more of a smart ass and less of an eager to please puppy like Fallon seems to be. I love all of the Matt Damon skits along with all the stuff Guillermo and the late Uncle Frank have done. I also have so much respect for him after what he did this past weekend – convincing Manny Pacquiao to let him walk out to the ring with him in order to troll Justin Bieber. I laughed so hard as I watched him walk out with Manny. It’s always hilarious when comedians manage to affect real-life events with their comedy – the Pacquiao/Mayweather fight was no comedy bit, it was a worldwide event watched by millions, and Jimmy found a way to sneak in and make it hilarious!


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The only thing about Jimmy Kimmel is that I feel he hasn’t really identified a brand of humor that is his own. He’s a hilarious smart ass, but that’s all I can think of when trying to decipher his style. With Dave you’re getting deadpan jokes, absurd skits and a talk show that isn’t a talk show, but a parody of a talk show. With Jimmy Fallon you’re getting gimmicky skits like I mentioned above. But with Jimmy Kimmel what do you get? I’m not really sure, but he’s funny as hell nonetheless.

It’s tough for people near my age or younger to really understand why Letterman is so funny. I think our perception is a bit off because we grew up watching Letterman tell absurd jokes and that was all we really knew. We never watched the old time hosts like Johnny Carson and therefore never knew how revolutionary Dave’s jokes were when compared to the old time talk shows. We thought that the “Will It Float?” was what happened on normal late night TV. The truth is, absurd sketches like that were invented by Letterman and were truly groundbreaking when they started; we just never witnessed the breaking of the ground. For Gen Y the ground was broken, the stadium was built, and there had already been 20 historic games played in it.

I read somewhere that a good way to understand Letterman is to realize he’s not hosting a talk show; he’s hosting a parody of a talk show. Everything he does is meant to make fun of the entire idea of a talk show. He’s making fun of the old-fashioned talk shows that were so rigid in their structure – a monologue, a couple skits, and a couple guests. Dave does those things but he makes fun of the whole idea in the process. Johnny Carson would NEVER stage elevator races at 30 Rock or have a Civil War reenactment on Broadway and 53rd.

I want to point out that Letterman is probably the most skilled interviewer out of all the late night hosts. Can you imagine Jimmy Fallon grilling Paris Hilton like Dave did in the video below?

Or how about the hilarious interview Dave had with Joaquin Phoenix? It turned out Phoenix’s interview was some sort of performance art for the film he was involved with called I’m Still Here.  Dave wasn’t in on the joke though and landed a couple great zingers. Check out the video below.

Even if you never understood Letterman or any of his jokes just try to kick back for these last few shows and remember, he’s not hosting a talk show. It’s a parody of a talk show. If you keep that in mind, you’ll laugh your ass off!


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If not, go watch Jimmy Fallon and drool on yourself.

Here are some more awesome Letterman clips for your viewing pleasure:

– Mike O’Brien