Veteran comic Greg Giraldo passed away yesterday at the age of 44. He had been in the hospital since Saturday, when he was found unconscious in his hotel room.

A Harvard-educated lawyer, Giraldo broke into comedy in 1999, performing regularly at the Comedy Cellar in New York City, and becoming a regular panelist on Tough Crowd with Colin Quinn in 2002. He made multiple appearances on The Late Show with David Letterman, Late Night with Conan O’Brien and The Howard Stern Show.

He was a frequent star of Comedy Central’s roasts, and had two stand-up specials on that network, in addition to three stand-up CDs, a role as a panelist on NBC’s The Marriage Ref and a judge on Last Comic Standing.

We spoke with Giraldo in the spring of 2006, just after the launch of Friday Night with Greg Giraldo on Comedy Central. He was gracious, funny, and smart—and not just when using the term “per se.” See our chat below.

-By John Bolster

You went to Columbia undergrad, Harvard Law School—and then ditched it all to do stand-up. What did your parents think?
They were thrilled. They encouraged it. It’d been their lifelong dream. All along, they wanted a son who would stand on a milk crate in a sports bar, entertaining drunks.

How did you fit in at Harvard?
I wasn’t part of that world, really. I lived off-campus. I went to law classes, but I wasn’t a Harvard person per se. Although I do say things like “per se.”

You wrestled Paul Reiser on an early episode of Comedy Central’s Friday Night With Greg Giraldo. Did you take him down?
It started, and then he didn’t fight back much. It just didn’t feel fair.

He’s in your weight class, though.
More or less, yeah. Sadly.

I notice you didn’t schedule Patrice O’Neal.
Yeah, I’m not an idiot. You don’t make it to have your own fake show, and then wrestle a monster the first week out.

Name a comic we’d be surprised to hear you like.
When I was starting out, a guy like Brian Regan—believe it or not—who’s squeaky clean. I’d never seen him before, but I’d never seen anything funnier live. He was just the funniest guy on the planet.

You recently toured with Dave Attell and Dane Cook. Any good stories?
I was sort of changing my lifestyle, so to speak—he says, with finger quotes: changing my “lifestyle.” I actually rented motorcycles with a friend of mine, and we rode between some of the gigs out on the West Coast. It was cool, but it was a lot more wholesome, you know what I mean? Hanging with Attell in Vegas is not the most wholesome approach to life.

You played Guantánamo Bay a few years back as part of a USO tour. Describe that experience.
It was hot. It was humid. And it got exhausting because we just kept driving back and forth, as close as we could get to the prisoners, singing “Hava Nagila” over a bullhorn.

[Laughs] Did they let you visit Cuba proper at all?
No. Well, that’s the whole reason we went down there in the first place. I mean, I’m all for being patriotic, but I was mainly going because I thought I’d be able to get laid for a bar of soap. It turned out that we were miles and miles away. Guantánamo Bay is all the way on the southernmost tip. And they moved all the whores.

They kept you separated.
Yeah, they did. You know what was pretty wild? I think things with Cuba are pretty stable right now. We got them kind of right where we want them.

Waiting for Castro to…
Yeah. I think Cuba is not as much of a threat to us as it might have been in the past. But they still have the fenceline set up, and they still have observation posts on either side. So you look across and you see these Cuban dudes just sitting in their towers. If you stay in those towers enough hours a day, you start thinking you still are in some crazy war. But it’s like, “Dude, you’re in a vacation place.” It’s like going to the Caribbean.

Not the Bay of Pigs or the Cuban Missile Crisis.
No. But apparently, not that long ago, they would harass each other, back-and-forth, across the fences. There were these tin-roofed barracks that the Americans had, and the Cubans would throw hangers all night long, wire hangers, over the fence so they would rattle down on top of the tin roofs. That would be wild if a nuclear Armageddon started with some drunk prank.

Speaking of laughable scenarios, in your act, you’ve noted that Georgia Governor Sonny Perdue had suggested closing schools as a way to save fuel. Then he actually did it for two days last year.
Why not? I’ve always said the schools are gas-guzzlers. We’re wasting our fuel on these kids. We’re also wasting a lot of liquid cheese. We gotta close down the schools and let the kids just roam freely. And instead of focusing on learning to read and write, they can focus on coming up with a renewable energy resource. Put ’em to work. Or maybe we can burn the kids for fuel.

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