For more than four decades, Kevin Nealon has built a career on making audiences laugh without ever seeming like he’s trying too hard. Nealon has become one of the most recognizable and respected voices in stand-up or chatting with celebrities while hiking up a mountain trail, he has mastered the art of making humor feel effortless. Fortunately for Cleveland audiences, he’ll soon return to one of his favorite comedy clubs when he headlines Hilarities Fourth Street Theatre from July 24-26.
Nealon became a household name during his celebrated nine-year run on Saturday Night Live from 1986 to 1995. Since then, the Emmy and Screen Actors Guild Award-nominated performer has remained a constant presence on screens big and small.
His latest stand-up special, Loose in the Crotch, is now streaming free in its entirety on YouTube, proving that his observational humor remains as sharp as ever. He’s also found an entirely different audience through his wildly popular YouTube series Hiking with Kevin, where nearly 400,000 subscribers tune in to watch him trade punchlines and surprisingly candid conversations with celebrities while navigating hiking trails.
CleveRock.com caught up with Nealon by phone while he was visiting Duluth, Minnesota—a city he was experiencing for the very first time—to discuss his latest projects, why inspiration for new material never seems to run dry, and how stand-up continues to provide a much-needed escape from life’s daily chaos, both for audiences and for himself.
For many comedians, finding fresh material can become one of the most difficult parts of a long career. After decades on stage, it’s easy to wonder whether the well of ideas will eventually run dry. Kevin Nealon, however, doesn’t see inspiration as something that has to be chased—he believes it’s everywhere. For Nealon, the challenge isn’t finding something funny; it’s simply paying attention.
“The well never runs dry. As long as you’re alive, you can come up with material. I come up with material just from everything. I come up with it from talking to somebody in the convenience store; maybe behind the counter. I’ll say something off of what he says and it’s funny and I’ll write it down. I’ll be with some friends, or at a dinner party, or reading a book, and something kind of sparks. You just have to be open to it.”
While Loose in the Crotch may already be available for fans to stream at home, that doesn’t mean Nealon is hitting the road with a set that’s frozen in time. Like many veteran comedians, he constantly tweaks, rewrites, and experiments with new ideas between performances. Audiences in Cleveland can expect a show that’s rooted in his signature style but continually evolving, with plenty of fresh material finding its footing alongside a few familiar favorites.
“When a lot of comics release their special, they kind of walk around saying, ‘Oh, start from scratch. I’ve got no material now.’ But I don’t know how effective that is. It’s certainly not going to work for a while on the road if you have no material. I’ll have a little material that’s old material, and the rest I’m working on and really kind of trying a lot of new things out. That’s really been going great. It’s funny when you really have to write, you sit down and you write. They realize they have the ability to do that or they’re just lazy. I admit that I’m lazy sometimes, too.”
What began as a simple idea has grown into one of Nealon’s most successful creative ventures outside of stand-up. His YouTube series, Hiking with Kevin, has attracted nearly 400,000 subscribers by replacing the traditional celebrity interview with something far less scripted: a walk through nature. The casual setting allows guests to let their guard down, leading to conversations that are equal parts hilarious, insightful, and wonderfully unpredictable.
“There was no original idea, really. It was just a happenstance. I asked my friend, Matthew Modine, who’s an actor from Full Metal Jacket and Stranger Things, if he wanted to go on a hike. I love hiking in the canyons around Los Angeles. We’re catching up, and the hike that we’re climbing is pretty steep. We’re both out of breath and we’re still trying to catch up and talk. I held my phone out and kind of did a self-tape. I started inviting more friends to hike with and I got a selfie stick and then put my camera at the end of it.
I enjoyed it more than anything. I wasn’t doing it to kind of create some kind of a viral thing, but it just kind of progressed. I ended up calling all my friends and hiked with all my friends I knew. It’s just like I throw out a big net. I’ll ask anybody to do it. I could ask Tom Cruise to do it or anybody. I don’t care if they say no, but I want to increase my chances of getting someone.”
{Sounds like CleveRock trying to score interview with big celebrities; cast a wide net and see who is agreeable. Maybe we should call Tom Cruise?}
CleveRock has spoken with many present and past cast members (now adding Nealon to our resume). The show has a reputation for being chaotic and unpredictable behind the scenes. Of all the SNL cast that CleveRock has had on the phone line (including Tracy Morgan, Colin Quinn, Michael Longfellow, the ensemble Please Don’t Destroy, among others), not a single person had a good behind the scenes story to offer. Nealon didn’t offer anything juicy, either. Lorne Michaels must have an ironclad NDA. He did, however, have a humorous anecdote about one particular episode.
“I’ll never forget when they were making a mask for me. They have to put plaster on your face and let it harden so they can make a prosthetic piece. I had to do Jay Leno, so they needed to build out my chin. And as it was healing, as it was warming up and getting harder, I passed out in the chair. Luckily I was able to work my way through that.”
The world has gone bonkers. The country is divided. People need an escape. Comedy rooms can offer that to patrons, even if only for a short time. The privilege is not lost on Nealon.
“I know what that escape is like because I’ve been on the other side of it many times and it’s a real welcomed escape. I know also, from doing stand-up comedy, being on stage myself, I escape it. I remember going through breakups; having relationships fall apart, and I would be devastated and I couldn’t get out of bed, but I would go and do my spot and it looked like I’d lost a lot of weight and I was bedraggled, but I would go on there and for that brief time of the day, I would escape my problems. Once I stepped back off the stage, the feelings would come back to me again. I think that’s kind of what it’s like for the audience, too. It’s a focus and it’s something that they want to let into their head. They want to laugh.”
Want to laugh with Kevin? He’s ready to come back to Hilarities, a place that he lists among his favorites to perform.
“Nick [Kostis], the owner, just loves that place, and loves what he does, and that’s kind of contagious. It’s got so much history to it and so many different unique rooms and events that happen there. I love the showroom itself. Everybody loves Nick and everybody loves that club, too. Sometimes you go to these clubs and you kind of dread it. But that club, it’s got a great green room and the people are nice in Cleveland and it’s always a treat. I always look forward to coming back there.”














© 2025 CleveRock Music Portal. A PROUD SHAPE CLEVELAND PRODUCTION