Why Gary Gulman Was So Miserable on Dane Cooks Tourgasm

When I remind Gary Gulman on this week’s episode of The Last Laugh podcast that this year marks the 15th anniversary of Dane Cook’s Tourgasm reality show, which first aired on HBO in 2006, the comedian replies, “I hadn’t thought about that. Wow. Are they celebrating it in any way?”

The immediate impression that he gives off is that he would rather forget about his time touring the country in what he now describes as a real-life Entourage starring Cook as a suddenly famous superstar surrounded on tour by his still-struggling comedian friends: Gulman, Robert Kelly, and Jay Davis.

What started as a hopeful bid to raise his comedy profile ended up being a pretty “miserable” experience for Gulman, who has since opened up about his struggles with depression and anxiety, most notably in his recent stand-up special The Great Depresh.

During our podcast conversation, I asked Gulman to reflect on this odd slice of mid-2000s comedy nostalgia, including the real reason that he briefly bailed on the tour midway through and almost didn’t come back.

Below is an edited excerpt from our conversation and you can listen to the whole thing—including stories about Amy Schumer, Jay Leno, Conan O’Brien and how he got from the psych ward to Carnegie Hall—right now by subscribing to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts and be the first to hear new episodes when they are released every Tuesday.

Where were you in your career at that time when you ended up getting the opportunity to be part of that tour and what ended up being a reality show, which maybe you didn’t know when you signed up to be on the tour?

I had just been on Last Comic Standing. So I had done some TV and was selling tickets on my own. But the interesting thing was that it dissipated really quickly. I was sort of back where I started after the show went off the air. It was short-lived. I mean, it was pretty much a summer and fall of being the flavor of the month. And then just going back to really hustling to sell even a small amount of tickets. And it was frustrating because all I wanted to do was to be able to tour and get out and earn my living as a stand-up comedian. And it was next to impossible, it was a real struggle. So that’s where I was. I had just come off Last Comic Standing maybe six months prior and we were shooting that show [Tourgasm], but it was on spec, as they say in show business when you don’t have any money. Nobody’s paying you to do it. Dane was just filming it on his own, and I guess planned to either sell it to his fans on his website or sell it to a network. And then by the time that tour was over, he was the flavor of the decade. I mean, people were going crazy to try and work with him. And so he sold it to HBO and they produced a series out of all this footage that, looking back on it, I had no idea anybody was ever going to see it. So I just was happy to be miserable the entire time.

What was your reaction when you saw it?

I remember thinking to myself, had I known anybody was going to see it, I wouldn’t have been so miserable and maybe I would have been on better behavior. But in the moment, I just thought it was kind of cool. And again, I was hoping it would help me to sell tickets. Robert Kelly and I went out on a tour [after it aired], but the show was about Dane and we didn’t sell that many tickets.

They wanted to see Dane.

They wanted to see Dane. I mean, show business is humbling on its own. And then you get these extra-special humblings. And so it was fun to be out on the road with Robert Kelly. We had a really good time. We had been waiters together growing up in Boston, doing comedy, so we had a really long history together. But it was really humbling. I was really trying to come to terms with the idea of being a sort of a Robin or a Scottie Pippen to Dane’s Batman or Michael Jordan.

Not what you imagined for yourself?

Well, in your thirties, in show business, it’s very competitive and your ego gets involved and that makes it very, very painful. So I’m glad I did it because if I didn’t do it, I would have regretted not doing it. But at the same time, I wish people hadn’t seen me being so unhappy. And I mean, I was really depressed on that tour, because it was just very hard to get any sleep and I couldn’t do a lot of the things that I did back then to maintain my sanity, like exercising and writing and trying out new jokes. And just being in somebody else’s orbit at that point in my career was not easy for me.

I mean, it was also a very bro-y vibe on that bus from what I can tell—

[Laughs] Yeah…

Which doesn’t exactly fit you as I know you now. So I’m wondering if you didn’t fit in very well with that scene.

Right, yeah, the interesting thing is that I look like a bro—

Visually, you fit in great!

Yeah, physically I’m a bro, but internally I’m more of the guy who works at the coffee shop and, and reads Camus late into the night.

“I’m physically a bro, but internally I’m more of the guy who works at the coffee shop and, and reads Camus late into the night.”

Then you sort of had a mysterious disappearance in the middle of the show, which they tried to mine some drama out of.

Yeah, they dramatized it. But the truth was I had a college gig that was paying more than the entire tour paid me.

That’s not good. That doesn’t speak highly of the tour.

Yeah, the tour was not very lucrative. That original one where we just went out, it hadn’t been sold to HBO yet. So I needed to accept the gig. And so I missed a couple of days and, I will say, I dragged my feet to get back on the tour. I held out as long as I could.

I was going to ask, how close were you to not going back?

I was on the phone to my manager asking them to get me a flight out of, I think it was Villanova, to go back to LA. Because I had reached my limits as far as how long I could stay on a bus sleeping with three other guys. And eating poorly and not getting any exercise. So, yeah, it was a nightmare.

Well, it’s quite a document of what comedy was like in 2005, 2006.

Yeah. I mean, in some ways it was sort of a real-life Entourage. It has a similar type of arc where this guy, who isn’t all that famous, all of a sudden he’s super famous and his friends were there to witness it. And I don’t know how well anybody handled it.

Next week on ‘The Last Laugh’ podcast: Stand-up comedian Taylor Tomlinson.

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