Massachusetts Funniest Person: Carolyn Riley.

Carolyn Riley is a brilliant young comedian originally from New Hampshire that has been a godsend to the Boston Comedy Scene.  After years of working out material at open mics and showcases she’s catching some major heat and leaving the competition in the dust.


Q: Recently Laugh Boston named you Massachusetts funniest person. Congratulations! How does it feel to receive such accolades from the biggest comedy club in the state?

A: Thank you! It was a whirlwind. I was never good at sports, but I am upsettingly analytical and competitive, so it felt good to let years of pent up energy out on stage. It has honestly been awesome seeing the positive responses from friends and family. You know you’re making it when Republican former classmates who stopped talking to you after the election follow you on instagram again.


Q: How did you decide to become a comedian? Where was your first show?

A: I got into stand up when I was in high school. I was running fundraisers as Class President. My uncle, Dave Rattigan produces shows in the greater Boston area and offered to help me book a show at my school. The first show we did when I was 16 was Steve Bjork, Steve Macone and Matt Donaher and I credit that show for making me want to try comedy. It wasn’t until I was 20 that I tried stand up, which was at a mic at The University of New Hampshire my sophomore year.


Q: Who were your biggest comedy influences?

A: My early comedy influences are actually entirely local to Boston. I started driving down to The Comedy Studio in high school all the time, the idea of getting booked there seemed like a pipe dream. Matt Donaher amazed me with how tight his writing is, and how defined his persona was. He was the first “alternative comic” I had much exposure to, so that’s what made me think I could try it without being a silly person. I also loved Andrew Mayer and Jiayong Li. I didn’t start paying attention to national comics until 3 or so years ago. My top all time would be Tig Notaro and Sarah Silverman.


Q: Is there any topic you try to avoid while on-stage?

A: I didn’t do any material about dating for the first two years, and I was super clean. I started in New Hampshire where stage time is limited, so if I wanted to work it was going to be a lot of clean family events. I didn’t want to be a dating material comic purely because I found it liberating to get to speak about myself on stage without any mention of a boyfriend (or lack thereof). I’ve talked a lot more about dating in the past year, but I still don’t discuss online dating. In my opinion if the fact that you met online isn’t necessary for the punchline, I don’t think it helps the joke. Hearing “online dating” just causes me to tune out at this point.


Q: What is the best gig you’ve ever had?

A: This past April I put a show together to celebrate the launch of my mother’s new art studio/classroom, The Art Room, in Newmarket NH. She launched business at a time where she was really overhauling her life and making a lot of big, scary changes. My brother and I wanted to give her a night to celebrate how brave and badass she is. Over 130 people came specifically for Janet (“Baby J”) and sold out the show. Dave “Uncle Dave” Rattigan hosted and provided all the tech. It was unreal getting to look out at the audience and see just how much more popular my mom is than me.


Q: And more importantly what is the worst gig you’ve ever had?

A: Any of the ones where the booker held the hug too long.


Q: Who makes you laugh the most right now?

A: Michael Che, Rory Scovel, John Mulaney and Ali Wong.


Q: What’s next for the funniest person in Massachusetts?  What would you like to achieve in the next year?

A:  I’d like to write and produce more sketches. I’m loving all the video content Boston comics have been generating lately. It’s also been really rewarding diving into another format to utilize material. I’d also like to get my time up to 45 minutes of college material so I can do more college shows. I am everything comics don’t like about college audiences: I am PC, have very little life experience, and I’m low energy.


Check out Carolyn Riley live at the Pourhouse this Wednesday at 8pm FREE.

Shawn is the owner and creator of

Leave a Reply

Your email address will not be published. Required fields are marked *