Henry Zebrowski (aka SNL’s “Naked Guy”) and the Sublimity of Rejection: How We Should All Aim to “Fail Faster”


Lemon Grove Essays

March 15th, 2025

Henry Zebrowski (aka SNL’s “Naked Guy”) and the Sublimity of Rejection: How We Should All Aim to “Fail Faster”

By Caitlin Morris

Listening to Last Podcast on the Left and its weekly true crime news round-up series, Side Stories, has been my audio comfort blanket for roughly seven years. The combination of horror, true crime, blue and bathroom humor, all created by three intelligent, empathetic, and unapologetically silly people, is the balm I need every Wednesday and Friday evening. I save the episodes for when I wind down from the day when it seems as if, on command, I crave something safely spooky and, to quote a Reddit commenter, a little “batshit.”

But January 22nd’s Side Stories episode, “The Audition,” did more than just provide sweet, sweet escapism. It was a revelation, at least for me, about the role failure and rejection play in one’s creative path and how rejection can lead to abundance.

Rather than the typical opening, a somewhat bananas riff on a true crime or esoteric headline, the show’s co-host Henry Zebrowski addressed the buzz around his appearance (a surprise to him) in Saturday Night Live’s recent SNL50: Beyond Saturday Night docuseries. In it, his audition was brought up as one of the most memorable failed auditions. Lindsay Shookus–a former SNL producer and talent agent–recalls Zebrowski’s audition and subsequent rejection in a somewhat acerbic tone. He’d come out on stage completely naked, pretending to be late for a meeting–-very à la Chris Farley. He was rejected, and later, Lorne Michaels told him, “We don’t do you anymore.”

Instead of becoming an SNL protéjé, Zebrowski kept working and soon landed a role in Martin Scorsese’s The Wolf of Wall Street and several TV roles. Most significantly, working on the margins, outside of mainstream spaces, eventually led him to his role as co-host of The Last Podcast on the Left, which, as of 2020, gets about 11 million listens per month. Not only that, but Zebrowski is also CEO of the Last Podcast Network, a multi-million-dollar company.

About this past failure suddenly resurrected and passed around the internet, Zebrowski said, “I realized that I’m happy….Every single thing that I tried to destroy about myself, or change about myself, that I wanted to make like somebody else is why I have this job now and why I have this life now.” And, listening to that resonated with me at a cellular level.

Much of the angst I feel as a writer comes from comparison. While nearly every encouraging meme quote tells us to avoid comparison, putting that into practice often feels impossible. And, the way my mind works around it is to take those comparisons and turn them into goals. Yes, I can get my prose to look like that with practice. I can recreate that feeling or that image if I just try hard enough. But Zebrowski undoes that thinking with such candid ease. All the parts of you you’re trying to carve away or shape into something you admire or yearn to be are actually the things that draw people to you, that make people want to pay attention to you.

This reminds me of a conversation with Lemon Grove’s Megan Nichols. We were discussing my podcast, Poirot Pals. I was throwing out ideas for ways to continue improving the show, but now I look back and realize I was trying to find ways to make it look and sound like every other show. Megan then gave me advice I still draw from for courage in both creative and social spaces: “People are already listening and returning episode after episode. Maybe you don’t change it. Maybe they’re drawn to what you’re already doing. What if you just kept doing that?”

What if we kept showing up as ourselves? And continued showing up and creating things that don’t fit, are misunderstood, that stand naked in front of a room of silent judges? Where would that take us?

Zebrowski ended his re-telling by saying, if anything, he wants to learn how to “fail faster.” Rather than avoiding failure and trying to worm and weave around it, he’s chasing it. Failure as prey. What boons are hidden behind its long teeth and gnarled claws?

Let’s go find out.

Caitlin Morris is a writer, editor, and educator with an MFA in Creative Writing from Western Washington University. She currently teaches writing and literature at Bellevue College and Highline College. Caitlin’s fiction has been featured in The Copperfield Review's historical fiction anthology, Halfway Down the Stairs, Jersey Devil Press, and Ghost Parachute. She is the cohost of the Hercule Poirot book club podcast, Poirot Pals.

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