Portfolio: Interview with Comedian Sean White (2016)

Editor’s Note:

This was one of my favorite interviews because it happened in person. Most of my interviews were conducted over the phone or through email. At the time, I was just an open mic comic and fledgling actor and I hadn’t even performed on a showcase in the city yet. Sean White was one of the veterans I looked up to and learned from. Sean took the time to recommend some books and gave me genuinely valuable insight into both comedy and the craft. I’m pretty sure I was the worst interviewer he’d dealt with up to that point, but I’ll always be grateful for his wisdom, time, and kindness. Originally published on BestComedyTickets.com, November 8th, 2015

Written by Gary Miller “There is a thin line that separates laughter and pain, comedy and tragedy, humor and hurt.” – Erma Bombeck

Chicago comedian Sean White has walked that line night in and night out. Highly respected by his peers and the press, Sean is a standout voice in the Chicago scene. He was named one of Chicago Magazine’s “16 Comics to Watch” and continues to carve out a unique space for himself with raw, honest, and thoughtful material that doesn’t flinch from life’s darkest moments.

Sean had been doing stand-up for five years when tragedy hit him like a freight train: first his sister passed, then his mother, then his brother, and then another sister. In the middle of all that, he got divorced. Most people would have crumbled—but Sean made a comedy album.

His debut, Dead & Gone, tackled grief, loss, and mourning head-on, transforming his heartbreak into something both brutal and funny. The AV Club recognized the work on its “Best Albums of 2015” list, and rightfully so. Dead & Gone isn’t just a comedy album; it’s a vulnerable, fearless exploration of what happens when the worst actually happens—and you still have to get on stage.

I caught up with Sean after a show at the legendary iO Theater, formerly Improv Olympic, tucked off Kingsbury Street in Chicago. The iO is always buzzing, a magnet for sketch and stand-up junkies alike. That night, the CostaCoast Cabaret & Variety Show, hosted by Costa Lapaseotes, lit up the Mission Theater—and Sean headlined, bringing the house down with newer material he’s workshopping for his second album, Angry & Alone.

He opened our conversation by riffing on failed military tech—specifically, the Japanese death ray. It was weird, specific, and oddly brilliant. It’s exactly how Sean works: smart, unexpected, and always a little dangerous.

He’s been grinding at a relentless pace, hitting multiple shows and mics a night. And his writing reflects that urgency. There’s no fluff in his act—it’s all precision, all earned.

When he’s not headlining rooms or tightening new material, Sean is building stages for others. He co-produces two weekly shows in Chicago: Tuxedo Cat, every 2nd and last Sunday of the month at Innertown Pub (Ukrainian Village, 7–9 PM), and Stand Up Stand Up, every Thursday night at the Crocodile Lounge in Wicker Park (9 PM). He’s also the co-creator of Beef, Chicago’s only comic insult show, which runs at the Laugh Factory.

That night, the poster outside the Mission Theater read:

“Sean White swings like a prizefighter, going in for the comedy kill with jokes that look misery straight in the eye.” — Chicago Magazine

I can’t think of a better description. Sean White doesn’t avoid the hard stuff—he makes it hilarious. And in doing so, he reminds us why comedy matters.

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