Audio and words by Lara Smith
How do you jump on a moving train? Better yet, how do you interview one?
This was the task I had set in my mind when I imagined interviewing John Tole. If you’ve ever seen him live or listened to his podcast, Whiskey and the Surfer, you know that John Tole is high energy, stream of consciousness, and a force that doesn’t need to be harnessed, just followed to its exciting denouement. You can imagine my surprise when I found him to be one of the most engaging and easily conversational interviews I’ve done.
Born and raised in the East Bay area of California, Tole grew up playing baseball. His skills on the field earned him a college scholarship. Though his education took a few turns–and three transfers–he earned a degree in philosophy, which should come as no surprise to anyone familiar with his work. Sports are obviously still a part of his regular vernacular: you’ll regularly hear “swing and a miss” on his podcast, Whiskey and the Surfer. Throughout each episode, you’ll also hear his philosophy at play, mingling his morning review of the Drudge Report with discussions of faith, life, comedy, and conspiracy. All this is set to a soundtrack of metal, punk, thrash, and an occasional slow track, that often gets the boot.
Tole explains his comedy beginnings back when he started showing up to open mics and working up the courage to sign up at The Comedy Store in La Jolla. No stranger to the stage, John Tole had already spent years playing in a band and cracking jokes in between songs, but it seems he had an inner desire to tell stories and connect with people in a way that comedy can fill like nothing else. Although the first open mic went well, he can clearly describe the first time he bombed on stage. It was a defining moment, giving him the “this is as bad as it gets” feeling of relief to keep going.
Tole spent three years in Dallas, but while considering a move to LA, decided the Austin alt-comedy scene felt like it might be a better fit for him. After six years in Texas, Tole decided to make that jump to LA. It wouldn’t be long before the Mile-high city was beckoning to him. John Tole now calls Denver home, with its thriving comedy scene. And true to form, he’s heavily immersed in that scene as he headlines the famous Comedy Works club at the end of this month!
John Tole’s knack to spin storytelling and crowd work together for unforgettable sets was a talent that had always marveled me. He makes it seem effortless, so I asked how he developed this skill. Tole says for about two years he focused on crowd work and going up and just talking to improve on his storytelling and being in the moment. That attitude of being in the moment was perfectly summed up in a conversation with fellow comics years ago as Tole says, “Do you realize no matter what we’re doing in our career, no matter how much money we make, we’re always just going to be hanging out in some version of a bar waiting to go on? We should enjoy this now!”