My best friend and I have an ongoing argument – it’s been going on for 25 years. He has a host of movies that he thinks are funny. They include several Adam Sandler movies – not the shitty ones now, but the classics. Happy Gilmore. Billy Madison. And then other “classics” like Zoolander and Tommy Boy. These are all classic comedies. I just don’t rank them at the top of my list.

The argument centers about the key question, “what is funny?”

Not to disparage those movies. They’re great and they are funny. They’re just not that funny to me.

What is funny to me is David Letterman.

51887407I grew up watching David Letterman and not the CBS version that most of you know – I remember watching his ill-fated daytime show where he would pull jokes out of a dishwasher. Then Late Night with David Letterman appeared during my high school years and dozens of VHS tapes were murdered trying to archive and rewatch classic episodes.

This was the sneaker wearing Letterman – the goof – the doofus – the joke teller. He came at his craft with a self-awareness and smarm that absolutely hit it on all cylinders for me. Letterman was funny.

Today will be filled with homages to Letterman – and rightfully so. But to me, Letterman will always be the home of monkey cam and guy under the seats and dumb ass jokes that were made hilarious by the delivery.

Here now, is my favorite David Letterman joke.

The year was 1987 and Letterman was doing a series of shows in Las Vegas. There were showgirls and Letterman wearing a Hawaiian shirt and those sneakers and it was insane.

Anyway, the joke goes… So I’m walking outside the casino today and a man stops me right in front of the door. “Excuse me, Mr. Letterman, can I borrow $100?”

And I stop and say, “Well, how do I know you’re not going to just take that $100 and walk into the casino and gamble it away?”

And them an stops and says, “Oh I got gamblin’ money.”

Watch the video below (Jump to 3:24 in the video below, or just watch the whole damn episode) and just watch the delivery. The timing. The cadence. And the side eye to the camera that says, “yeah, this is a dumb joke. But that’s what I do. Tell dumb jokes.” And you have no choice but to laugh your ass off.

That’s Letterman. That’s why today is so special. That’s why his show was so special to me.

And that is what’s funny.

Good luck, Dave. You’ll be missed.

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