Stephen started doing stand-up comedy in Hampton Roads Virginia in 2013. Making his way through the open mic scene he soon found his way to the Funny Bones in Richmond and Virginia Beach. A four-time winner of their Clash of the Comics competition Stephen became a regular performer at both clubs as well as a host Cozzy's Comedy Club in Newport News. He performed nightly at those clubs and bars all around the scene until moving to NYC in 2014.
Stephen has been living in NYC since July 2014 performing at clubs and venues all over the city, including Broadway Comedy Club, New York Comedy Club, Eastville Comedy Club, Gotham Comedy Club, Caroline’s, and several others. He’s produced several open mics and shows in the city throughout the years, most notably in 2018 coproducing Popped Collar Comedy every Saturday with Dan Wickes. He was passed at New York Comedy Club in 2018 and performed there nightly until recently. Now you can watch him bored in the house on all social media platforms under Stephen McLonghair Bolles. Though not his legal middle name, it narrows the search engine significantly.