After more than four decades in comedy, Kevin Nealon remains a rare constant: sharp, curious, and still evolving. Best known for his nine-season run on Saturday Night Live, Nealon has long since moved beyond legacy status, continuing to surprise audiences through stand-up, storytelling, and projects rooted in genuine curiosity.
His new stand-up special, “Loose in the Crotch,” which premiered January 27 via 800 Pound Gorilla Media on YouTube, finds Nealon at his most confident and unguarded. Across the hour, he delivers deceptively dry observations with impeccable timing, taking on everything from skydivers who break the sound barrier to overeager coffee servers, runaway Roombas, awkward Uber texts, and the frustrations of self-checkout. Nealon also explores the life-changing power of his TOTO bidet, the loss of a beloved cat and the questionable decision to bury him with the perfect pair of jeans, alongside hospital standoffs, stress-eating entire cookie trays, and the philosophical question of what food is actually worth bending over for after a certain age. The result is a sharply observed, absurdly funny hour packed with big laughs and instantly quotable moments.
Nealon’s creative output extends well beyond the stand-up stage, as he continues to expand his reach across a wide range of projects. That spirit carries through his long-running digital series, “Hiking with Kevin,” recently licensed by FOX Nation, where candid conversations unfold far from the confines of a traditional interview. It also extends into his work as an executive producer on Apple Original Films’ “Come See Me in the Good Light,” now streaming on Apple TV+, a project that highlights his instinct for thoughtful, character-driven storytelling.
Beyond the stage and screen, Nealon is also the author and illustrator of “I Exaggerate: My Brushes with Fame,” a reflective collection of caricatures and essays that offers a more personal look at the relationships and experiences that shaped his life and career. With the “Loose in the Crotch” tour underway, Nealon remains focused on the craft of comedy and the creative instincts that have guided him across decades in the spotlight.
Icon Vs. Icon’s Jason Price caught up with Nealon to talk about the new special, creativity, longevity, and why he continues to find new ways to surprise both himself and his audience.
Hey, Mr. Nealon, how you doing today?
Pretty good, thanks. How are you?
Very well, thank you. Thanks so much for taking time out to talk to me, especially on the day you’re new comedy special, “Loose In The Crotch,” is being released into the wild.
Absolutely!
First of all, thanks for all the hard work you put in through the years. YMy friends and I grew up watching you. It was you and your peers on Saturday Night Live became a huge focal point of our lives growing up. So here we are, all these years later, and you’re still rocking it!
Still rockin’! [laughs] Thank you, man. I love what I do. I think that’s a huge part of it,. You know, I have old high school friends who ask me, “Kevin, when are you gonna retire, man? Why are you working so hard?” I tell them that I don’t even consider this work. I love what I do.
That’s awesome and one thing I love about you creatively is that that passion shines through in everything you take on.
Kevin Nealon: Wow, thank you. I really do love this. I have so many interests in life, and I’m never at a loss for something I enjoy doing. I love to paint, I play guitar and banjo, and of course I love comedy. I enjoy hiking, too. I just really love my life.
How did you get involved with the arts early on in life?
Well, when I was growing up, I always pictured myself being in a band. I wanted to be a guitar player, or like James Taylor, or Crosby, Stills, and Nash. I was in a lot of garage bands, but it just wasn’t clicking for me. Then I thought maybe I’d do coffeehouses alone with an acoustic guitar, but I was too shy to sing on stage, and I probably wouldn’t have been that good anyway.
Comedy came easy to me. I would memorize jokes and tell them at parties, and friends would always say, “Hey, you should go into New York and try some of those comedy clubs,” because they were just starting to pop up then. So I went in and checked out a place called Catch a Rising Star, which is defunct now, and it was incredibly intimidating. There were so many people crammed in there, everyone was smoking, this was back in the 1900s, and there was a real barrage of comics on stage. I remember thinking, “Oh man, I can’t do this here.” So I went out to L.A. instead. Psychologically, I’m not really sure why I felt the need to make people laugh, but I really enjoyed hearing that reaction from people. That was kind of what it was.
What was it about stand-up that really spoke to you early on and ultimately made you want to pursue it?
I saw it as a craft. I was really impressed by how someone could come out on a TV show for five minutes and present this incredibly well-crafted monologue that held people’s interest and made them laugh. I thought, “That looks like a great job.” I already liked telling jokes, so now I just had to learn how to write my own. That was really the first step.
Once you landed in L.A. and started getting your feet wet in the stand-up scene, what was that world like at the time, and how difficult was it to navigate as a young comedian?
Yeah, it was all very new to me. All I ever wanted to do was stand-up comedy, so I drove out to Los Angeles with a friend of mine from college named John. He didn’t know I wanted to do stand-up. He thought we were just going out there to explore and experience California.
The first place we went was the Improv in Hollywood. Budd Friedman was the owner at the time, and it was the afternoon, so I was just standing there looking in through the windows, thinking, “Wow, this is the Improv. This is where Andy Kaufman, Jay Leno, David Letterman, and all those comics performed.”
All of a sudden, the door opens and it’s Bud Friedman, the owner, the guy who really helped shepherd in stand-up comedy with the brick wall behind you. He asked, “Can I help you?” I said, “Oh my God, I was just curious about the club. I’m from the East Coast, and I’d always heard about it.” He said, “Well, come on in, I’ll show you around.”
He showed me articles on the wall and then took me into the back showroom. My jaw just dropped. I said, “That’s the stage?” That was the stage where all these comics I’d watched on TV growing up performed and developed their acts. We made a little small talk, and as we were leaving, he said, “Well, come back and see us again.” And I did. I came back there almost every night for the first 10 years.
That’s ambitious!
That’s really where I got my start, at that club, and I also bartended there for a couple of years. After that, I went down to San Diego for a couple of months with my friend John, and we just kind of hung out. We both ended up becoming department store Santa Clauses through a temporary help agency because we couldn’t find jobs. I was probably the worst Santa Claus you’ve ever seen. I was about 24, skinny, wearing a cotton beard. The costume was awful. They were very serious about taking pictures and making money, and they even Scotch-guarded our Santa pants because they knew kids would pee on them since they were scared. Sure enough, I watched the pee roll right down my pants onto the floor like something out of an animated cartoon!
Eventually, I came back up to Los Angeles and started hitting all the open mic nights. As far as the atmosphere back then, there really weren’t a lot of comics. I’m guessing maybe 50 in L.A., maybe even in the whole country. I knew every one of their acts because I watched them so many times. I knew when they were going to swallow, when they’d take a breath before the punchline.
Back then, when you started out, you were emulating someone. There were a lot of comics emulating Richard Pryor, Black comics especially, Jewish guys emulating Woody Allen, people like me gravitating toward Steve Martin or Andy Kaufman. Now, there’s been such an influx of stand-up. It’s become accepted as a real career. It’s not such an exclusive club anymore. Everybody’s doing it, and a lot of them are funny.
There’s also so much more access now through social media. Back then, there was only one late-night talk show that mattered, and that was “The Tonight Show” with Johnny Carson. That’s how you got validated as a stand-up. Now there are tons of late-night shows and endless platforms online, which really opens the arena for a lot more comedians.
You were doing it night after night for so long. When do you feel you really came into your own, found your creative voice, and started firing on all cylinders?
It was a gradual thing, very gradual. Eventually, people start talking about your material and even quoting your jokes. I think when I got “The Tonight Show” with Johnny Carson for the first time, that really validated me as a stand-up. It gave me confidence and completely changed the trajectory of my career. I started headlining clubs and having openers for me instead of opening for other people. That was probably the moment I realized things were really taking off.
Was there anyone in the scene you were watching or working alongside at that time who really helped keep you inspired as a young comic?
I learned from so many comics. Like I said, I bartended at the Improv, so I was there all the time, and I’d see these comics come in that I really enjoyed and was a fan of. Every night I’d watch them perform and take it all in. That’s how I learned, by watching. And I loved it. It never even felt like work to me.
There were comics like Jay Leno and Richard Lewis who I watched closely. Andy Kaufman was a huge influence on me because he was so unique, so different, and so interesting. He played so much with the audience’s mind, taking them in one direction, leaving people unsure of what he was doing, and really pushing boundaries. I also watched Seinfeld perform because we came up around the same time, more or less. There were so many of them.
As a young comic, you were learning constantly. What lessons about the business did you pick up back then that still resonate with you today?
It’s a business, so you can’t take things personally. I learned that a long time ago, and things don’t really affect me that much anymore. I think even in regular life, I’m not easily shaken. I don’t want to say I’m dead inside, because I’m not, but I’ve just gotten used to a lot of rejection and disappointment, especially in the early stages. Not so much now. Because of that, nothing really bothers me too much on that level.
You’ve got a brand new special out now. It’s been a little while since the last one. What made now the right time, and how did the ball get rolling on this new special?
The special is called “Loose in the Crotch,” and it’s on YouTube through the 800 Pound Gorilla platform. I really love it. You’re right, it had been a while. It’s been about seven years since my last special, and this one is my third. I wasn’t really interested in doing another special for a long time. I was enjoying what I was doing and thought, why go through that whole process again? But it eventually got to a point where I realized I had a lot of good material, and if nothing else, I wanted to document it and get it out there on a platform where people could see it. That was a big part of the reason. I also wanted to move on creatively. I wanted that obligation and pressure to write new material and keep things fresh for myself, too.
I filmed this one at the Irvine Improv. It’s a really beautiful theater that seats about 500 people and still has a great club atmosphere. I see a lot of specials where comics come out onto these huge stages with flashing lights, and that’s fine, but it’s just not my thing. My stand-up is a little more conversational, and I prefer a more intimate setting.
Honestly, my favorite venue for comedy is a dinner party. Sitting at a table with maybe eight people, jumping in, interjecting, and bouncing off their ideas. That’s what I enjoy the most.
That’s awesome. You’ve got a tour coming up in support of this as well. After doing this for so many years, how do you keep things fresh on the road? I imagine it can still be a bit of a grind, even these days.
Yeah, it can definitely be a grind. I think a lot of comics would agree that we’re basically paid to travel. The stand-up itself is fun, but getting there can be challenging, especially in the winter with bad weather and flight cancellations. But I love stand-up. It’s all I ever wanted to do, Jason. When I first started out, I didn’t care about being on shows like “SNL” or “Weeds.” Acting wasn’t really on my radar. I remember watching the acting troupe in college and thinking, “Wow, those people really need a lot of attention.” And then I ended up getting into it.
Stand-up is what I truly love. Even with this many years under my belt, I still love it, and I probably always will. An audience laughing is incredibly empowering to me. It reinvigorates me and makes me feel alive. Being on stage is also a great escape. I’ve gone through difficult times in my life, and when I was on stage, I could completely forget about all of that. It was like being inside a bubble. During the pandemic, that was especially hard to lose.
When you look back at your career as a stand-up, which now spans decades, how do you feel you’ve most evolved?
When I started out, I was emulating other comics, just like everyone else does, and then I eventually found my own voice. Seeing the consistency of that over time was kind of magical to me, watching the results of it. It’s a gradual evolution. It reminds me of a blues guitar player. The more struggles they go through in life, you can hear those changes reflected in their music. A lot of it wasn’t really recognizable to me in the moment. Things just seemed to happen the way they were supposed to. It’s like aging. All of a sudden you’re 80 and you think, “Wow, how did that happen?”
Now, I’m much more open creatively. I’m more willing to take risks on stage, to explore new material and different directions instead of sticking rigidly to a set list of bullet points in my head. I feel freer to go down different avenues of possibility, always knowing I have my surefire material to fall back on.
It’s been very cool to see you branch out in new creative directions. Your work as a caricaturist is amazing. Tell us a bit about that side of your life.
Thank you. I love painting, drawing, and sketching, all of it. When I was a kid, I found a napkin someone had left behind in a cafeteria with a really cool drawing of a guy with a big nose and chin. I thought it was great, so I kept copying it over and over until I could do it myself. That’s really where my interest in caricatures started.
Growing up, there were two framed caricatures of my parents hanging on the wall. They were done by a Parisian artist when we lived in Europe, and they were really good. I think, subconsciously, I studied them all the time, looking at the curves and how features were exaggerated. That definitely stuck with me.
Even on “SNL,” I was always sketching. I’d draw in the margins of scripts during table reads, sketching Farley across from me or whoever was nearby. Then, about seven years ago, maybe a year or two before the pandemic, I started following really talented caricature artists on Instagram. I studied their styles, developed my own, and started getting more technical, adding color and refining the work.
Eventually, I had built up a large collection, and a woman approached me about doing a book that would feature the caricatures alongside short anecdotes about the people, whether it was Chris Farley, Dana Carvey, or others. That became “I Exaggerate: My Brushes with Famee.” It’s been doing really well, and after that, people started asking how they could buy my artwork.
I never really had an outlet for it before. I was just doing it because I loved it. But recently, I created an online store at KevinNealonArt.com, where people can check out different options and purchase the work.
When you sit down to create one of these pieces, what’s the process that takes it from idea to finished work?
It’s kind of a multimedia process. I usually start by sketching with pen and paper, then I move into a digital phase where I paint and build it up there. Once that’s done, I’ll go back in and paint over everything again. That’s basically the process. I also still sketch a lot just with pen and paper on its own.
One thing I really like to do, Jason, is sketch people when I’m flying. I fly a lot, so I’ll draw the people sitting across the aisle from me. A lot of those sketches ended up in the book. Usually they’re sleeping, so their faces are kind of frozen like that, and it makes the time go by really fast.
What were some of the big challenges of putting project like this book together? Did you learn anything through that process?
Yeah, I definitely did. It was a lot of work. I learned that pretty quickly. I was basically locked in my studio for eight or nine months, just doing one piece after another because of deadlines. I also realized how much people really love art. When they see something like that, they genuinely connect with it, and that made me really happy. During the pandemic, I was doing these caricatures and posting them, and it became an outlet for me creatively since we couldn’t perform comedy in clubs. It felt like a kind of nonverbal comedy. People really started latching onto it, enjoying it, and getting excited to see each new piece. I also have an Instagram, KevinNealonArtwork, where you can see a lot of my paintings.
That’s very cool that you have all these outlets.You’re multi-dimensional.
I am multidimensional! that’s true, that’s true.
What else do you have cookin’?
My wife and I are executive producers, along with a team of other executive producers, on a new documentary called “Come See Me in the Good Light,” which was recently nominated for an Oscar. We’re incredibly excited about it. The film won at the Sundance Film Festival and then received the Oscar nomination, which is something I never would have imagined happening in my life. From the very beginning, Tig Notaro was involved. She’s a close friend of mine and one of the producers, and she’s the one who brought us into the project. She told us about it early on. At its core, the film is a love story between two poets, Andrea Gibson and their partner, Megan Falley. Andrea is facing a diagnosis of inoperable cancer and doesn’t have long to live.
What’s remarkable about the film is that it’s not a typical tearjerker, although there are certainly sad moments. It’s surprisingly funny, uplifting, and full of hope. It shows how Andrea faces this diagnosis with joy, what she calls radical joy, and offers a powerful perspective on life. It really makes you think differently, gives you hope, and reminds you of our mortality.
What do you look for in projects and material when you’re deciding where to invest your time and creative energy?
I look for quality first. I’m drawn to things I can relate to, material that strikes a chord with me and that I believe will also resonate with an audience. I’m also interested in projects that feel different and unique. And of course, working with good people is always important.
As we start to wrap things up, I did want to ask about your time on “SNL.” What was day one, week one like when you landed that job, and what did that moment mean to you in your career?
Well, Jason, it all happened very quickly for me. I was a stand-up comic, and I still am. Dana Carvey, who’s a friend of mine, got on the show and recommended me. Lorne Michaels flew me in for an audition, and I passed, so they hired me. It moved so fast that I barely had time to tell anyone I was on the show. I think I found out on a Friday, and by Monday I was in New York with my bags packed.
It was also a strange time because the year before, they were talking about canceling the show. They kept it on a little longer, but none of us knew how long it would last, so we were basically living out of our suitcases from show to show. Still, the energy and excitement were incredible. Being in that studio was unbelievable. You’d hear about people like John Belushi and Gilda Radner, and then suddenly you’re there with Dana Carvey, Dan Aykroyd, all of them. It was surreal.
I ended up spending nine years on the show, and the experiences from that run were amazing. I got to work with some of my heroes, people I grew up listening to and admiring, like Paul Simon and James Taylor. I worked with Steve Martin, and even legends like Charlton Heston and Robert Mitchum. It was a pretty spectacular experience.
A life well-lived! It feels like there’s so much there to explore. Do you see yourself writing another book someday, maybe diving into those experiences?
Yeah, definitely. I have at least one more book in me, probably another art book. And as my life continues, it’s been really interesting, so maybe someday there’ll be another book that explores that. The book, “I Exaggerate: My Brushes with Fame,” is kind of a memoir for me. I’m sketching different people I’ve encountered throughout my life and writing about what those people meant to me or the experiences we shared.
You’ve also got yet another creative outlet with your ongoing “Hiking With Kevin” series.
Oh, absolutely! I like exercise, and when I first started doing this, I had no plan to turn it into a hiking podcast or series. I was just hiking with my friend Matthew Modine, and we started having these funny, interesting conversations. I had my phone in my hand, holding the camera, and it was very rudimentary. I remember thinking, “This is funny,” so I posted a few clips on Twitter at the time.
At first, they were just little two-minute segments. Then I started making them longer, and now they’re about 20 minutes each and live on YouTube. I really love it. I’ve had so many great guests, like Conan O’Brien, Tom Hanks, and Sheryl Crow. I’ve done about 170 of these hikes so far.
Yeah, it’s wild. It really pulls back the curtain on you and on some of the talents we all know and love, all within a unique and relaxed setting. It’s definitely worth tuning in for!
Thank you!
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My pleasure. I know we’re short on time, so one last question. You’ve been a real inspiration to me. What’s the best lesson we can take from your journey as an artist?
It goes back to what we were talking about at the start of our conversation. Enjoy what you’re doing. Otherwise, you might as well not do it. When you have a real passion for something, you don’t mind working hard at it. And it’s important to stay engaged with the people around you in that community, because a big part of creativity comes from bouncing ideas off one another.
Last but not least, what should we be on the lookout for from you as we move further into 2026?
I’m leaning toward doing another book, so I’ve been creating a lot more caricature paintings. I’m also touring with a new schedule and a new tour called “Feel the Flow,” which is a line I said in “Happy Gilmore.” I also have a couple of movies that I’ve already shot that haven’t come out yet, and I’m really excited about those.
As a fan, thank you for all the hard work you put in. Thanks so much for your time today. It really means a lot.
Thanks a lot, man. I really appreciate it. This was a great conversation. Talk to you soon!
Don’t miss Kevin Nealon’s latest stand-up special, “Loose in the Crotch,” streaming free on YouTube via 800 Pound Gorilla, and visit kevinnealon.com for the latest tour dates.
Jason Price founded the mighty Icon Vs. Icon more than a decade ago. Along the way, he’s assembled an amazing group of like-minded individuals to spread the word on some of the most unique people and projects on the pop culture landscape.
