Stephen Bolles’ Comedy Hits Every Note
By Matt Levy
Sometimes at a comedy show, audience members will see comedians hanging out in the back of the room before the show starts. The group of comics distancing themselves from the crowd always make for an odd bunch. There will be a studious one writing in the corner, a few buried on their phones and some laughing together and busting each others’ chops. Stephen Bolles is the one always in the middle of the action. He’s the comic you want to hang out with before the show and after; the performance onstage that comes with a hip hop flair, a flip of his long hair and a mix of beatboxing is not just an act. Bolles is funny all the time. However, to become that guy doesn’t just happen. It takes a lifetime of getting comfortable being the funny guy and that is who Bolles is through and through.
I spoke with Bolles to learn a little more about who he is offstage. Who is that long haired dude that just made us laugh and where does he come from? Well, he actually comes from a military family; his mom is a retired pilot, who flew for the Navy and commercially for Pan Am and then United for 31 years. His father is a retired Marine, and he’s been an elementary school principal for at least 20 years. You wouldn’t exactly expect the fun-loving comic to come from a family of Marines and Navy vets but Bolles said he had a “Pretty normal childhood growing up on a cul-de-sac in northern Virginia with his family and a ton of neighborhood friends.” He grew out his hair in middle school because he loved metal like System of a Down, Slipknot, and Marilyn Manson. Like I said, not exactly your typical Marine’s son.
At that time, Stephen’s life was all about music. He was a music major in college playing electric and standup bass. Before he attended Christopher Newport University, he did something pretty special that would hint at a future in comedy. One of Stephen’s favorite performances ever was in high school for his departing band teacher who was transferring schools. During an award ceremony at the end of the year, Bolles did a surprise performance for him. It was a parody of a Jay-Z song entirely about him and the program he built. The teacher was a big Jay-Z fan, and Stephen had a real band playing behind him, all friends from marching band. Bolles said, “(That) was probably the most personalized comedy I’ve ever gotten to do, especially since it was RIGHT in front of him, and the whole school. I don’t wanna say I peaked in high school but aside from roast shows I’ve done (which are MUCH meaner), I haven’t gotten to dedicate a comedy project to someone in such a meaningful way since then.”
Back to Stephen at college. He found out early on that the school didn’t have a jazz degree and he would have to spend three hours every other day in an orchestra churning out whole notes on an instrument bigger than him. Even though he loves music and plays to this day (he says, “I paid too much for reeds and instrument repairs to not still use that side of my brain”), it was then that Bolles dropped the music major all together. “Fuck orchestra,” he said. He was also making his transition to mumble rap.
Oddly enough, that’s when his comedy career began. The Virginia native who has been in New York for six years told me that he “was a big band geek and always loved Weird Al.” He said he’s been a fan of the wild-haired parodist since he was nine. Dude stans hard. As for his stand up, Bolles said when he began he thought he was going to be a funny musical act, until he went to his first open mic in college and realized it’s a lot easier to have fun when you don’t have to carry around instruments. Stephen likes to say, “Good decisions rarely make for good material” but he made the right call here. It should also be noted that he attributes that quote to himself, a self-proclaimed “guy who had a minor overdose in 2019.” Makes for great material.
Influenced by comics as wide-ranging as Bill Burr, Dane Cook and Jim Jeffries, he took the stage. He hasn’t stopped since. Bolles got real with me for a minute in the interview and said, “Making people laugh, it’s the best feeling on earth. Really resonating with someone in a way they hadn’t considered before.” Around 2014, he made his way out to New York City to try and make it in comedy. It’s not easy at first and you can get lost in the fray. That’s what makes it so special once you feel as good as Bolles does these days onstage and off. However, he said what kept him going was when he was, “Feeling like a nobody in NYC, then going back to the VA Beach Funny Bone in 2017 on vacation and crushing a sold out room. Made it all feel worth it!” Since Bolles started coproducing a consistently sold out show with Dan Wickes — The Popped Collar Comedy Show— at The House Party Cafe in Bushwick and performs regularly at New York Comedy Club.
Since COVID-19 hit, Stephen has been at his uptown NYC pad in Inwood with his wife. Their place is spacious, with enough room for their three cats — save for the poor acoustics where they can hear every sudden movement from upstairs neighbors. They don’t mind though; they’re newlyweds, having married in March of this year. His wife is from Spain and they met at a cafe Bolles was working at in 2017. The second time she came in, they talked for four hours. Stephen added, “She says she didn’t understand English very well back then, which is why I was so much more fun to talk to than I am now.” These days at home Stephen is learning Spanish to keep up with her so he can keep up with her secrets. He joked, “Anyone who’s been in a mixed-language relationship gets what I mean.” On top of that, Stephen is filming impressively choreographed videos that showcase his comedy, music and mumble rap skills all at once (you can find all of this as well as stand up clips at his YouTube channel linked below). In fact, go check the channel now and see the musician-turned-comic utilize all of his talents in a setting outside the Club he’s so comfortable in. You’ll want to stay on the social for awhile and hang just like you would in real life.
You can find Stephen in these places:
YouTube: https://www.youtube.com/channel/UCjvHmUthD1LmKdDjKuWdDfw
Twitter: https://twitter.com/McLonghair
Instagram: https://www.instagram.com/stephenmclonghairbolles
And don’t forget, like Stephen always says, “Don’t eat the butt until you eat the front. Manners are important.”
