- Gary Gulman

I had no idea Gary Gulman cared so much about philosophy. But it shouldn’t have surprised me.

I’ve been a fan of standup comedy for as long as I can remember. My earliest impression probably came from watching Ed McMahon introduce comedians on Star Search. I have this foggy memory as a kid that I couldn’t believe standup comedy was even a thing: everyone pauses to listen to one person whose sole purpose is to say things that make us laugh. How could anyone not want as much of that as possible?

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In the summer of 2004, I was heading into my final year of my master’s in theology. I had watched the premiere season of Last Comic Standing the year before and thought it was so-so, but I gave the second season a shot. My favorite comedian on the show by far was a young Gary Gulman, who grew up on the north shore of Boston, which is a stone’s throw away from where I went to college. Gary’s style was so fresh; smart, positive, and just so well-written. A couple years later, I saw him appear in a documentary where he toured around the country with Dane Cook, who at the time was as big of a standup as anyone had seen since Steve Martin. And a year later in 2007, I finally got to see Gary in person at Helium Comedy Club in Philadelphia, performing with Philadelphia native and LCS colleague Todd Glass. The show was brilliant.

Since first seeing him on Last Comic Standing over 20 years ago, Gary has always been one of my favorite standups. I would regularly show people his bit about The Karate Kid from his 2012 special (available on Prime), and was surprised with most of his fan base to hear about his intense struggles with depression that he reveals in his 2019 special, The Great Depresh.

But it wasn’t until his 2023 special, Born on 3rd Base, when I learned about a personal connection. I thought that special was one of the best he’s done, so for some reason that I can’t explain I paused at the end of the special to see who he thanked, and noticed a familiar name at the end: Tom Ryan. Tom was my third guest on the podcast, where you can hear the story of how he and I met. I took a picture of the Thank You screen with his name on it and sent it to Tom, and he mentioned that if Gary ever made a tour stop in my area, to let Tom know and maybe Gary and I could connect. That generosity from Tom blew me away.

So when Gary had a show here in North Carolina (see if he's coming to your area), I made sure to be there, both to see the new show and to see if there was any chance I could say a quick ‘hi’. I will always remember what happened next: Gary was not only nice enough to say hi, but the first thing he said was, “You have that philosophy podcast, right? Let’s do the podcast!” You have to understand, most people express zero interest in philosophy, and here was this top-tier comic telling me they’re into talking about it with me?

So here is that almost-2-hour conversation. You’ll hear about Gary’s interest in philosophy and why he thinks it’s important, but so much more about how he looks back on his career, his ethics of comedy and life, and what he’s working on next (I can’t wait!).

Until next time.

Jared

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