Watch
Long-form interviews below. New clips go up on Instagram and TikTok most days.
About
Gary Bolles grew up in South Boston in the eighties and nineties and didn't get on a stage until he was forty-three. He started going to open mics, and turned the reps into paid work across New England — Nick's Comedy Stop, casino rooms, supper clubs, VFW halls and private parties.
The act is Boston: family, marriage, the neighborhood, and the particular way people from here argue with each other. He works clean when the room needs it and doesn't when it doesn't.
He also does crowd work for a living. Between gigs he guides trolley tours around Boston — forty strangers at a time, eight hours a day, working clean and keeping a bus laughing from Southie to the North End. Most comedians get that many reps in a month.
Upcoming
New dates are announced on Instagram first
Get an email when Gary books a date near you. No spam, no newsletter — just dates and presale links.
You'll get an email when Gary books a date near you. Nothing else.
Selected Appearances
Press & Media
Boston commercial radio, a Southie outlet, and five independent shows that each booked him as a guest.
“Comedian (and Southie native) Gary Bolles performs at Broadway Golf Club.”Caught In Southie · June 14, 2026
On The Radio
Podcasts & Interviews
Book Him For
Host, feature or headline. Brings his own crowd.
Clean set, tailored to the room. No inside jokes about your CFO unless you want them.
Birthdays, anniversaries, retirements, backyard tents.
Comedy nights that need to raise money and still be funny.
Hosted Ma$$hole in One at Broadway Golf Club for a Will Noonan headline set — and works a trolley full of tourists most days of the week. Clean, quick on his feet, and used to winning over a room that did not come to see him.
Book Gary
Fill this out and it comes straight to Gary with everything he needs to give you a real answer. Replies within 24 hours. Or email him directly at sonofsouthie@gmail.com.
Gary reads every one of these himself. You'll hear back within 24 hours.
If it's urgent, email sonofsouthie@gmail.com directly.
Photos
Press and promo photos available at full resolution on request.
On Stage & On The Road
Follow
Same handle on Instagram, TikTok and Threads. He built the audience before he built the act.
