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‘Big Irish’ Jay Hollingsworth plots his return to Massachusetts

The Los Angeles-based comic plays three shows at Worcester's WooHaha Comedy Club this weekend before hitting Laugh Boston

Via the artist

He started his stand-up career in Boston, and he’s known to rock Celtics green — so it’s pretty safe to say that New England grit courses through the veins of “Big Irish” Jay Hollingsworth.

Making his return to the Bay State to take his first crack at the WooHaha Comedy Club crowd in Worcester for a trio of shows this Friday and Saturday (March 1 and 2) as well as the free-of-charge Bloody Good Comedy Brunch at Laugh Boston on Sunday (March 3), Hollingsworth is looking forward to coming back.

While originally from the northwest, Boston was where it all began for Hollingsworth, and even after having the chance to work spots like Nick’s Comedy Stop, The Comedy Scene at Patriot Place, and Laugh Boston over the years, the idea of coming back to New England never loses its zeal for the now Los Angeles-based comic.

“I’ve heard great things about the WooHaha, like how the neighborhood loves it, and how the comics who have worked it think it’s great, so I’m excited to get there,” Hollingsworth tells Vanyaland. “I always love coming back to Boston too. I moved to Seattle after getting laid off from a job in Boston years ago, and then I moved to LA after that, but I’m always going to love coming back to Boston. I love the people, I love the history. I love pretty everything about the city.”

While maintaining the ability to carry on a true east coast spirit with his Boston-bred brand of stand-up while living on the west coast, Hollingsworth is keeping himself busy on the side with a couple of projects that are sure to make an impact in the comedy community, and beyond.

Alongside his friend and fellow comic, Kevin Fredericks, Hollingsworth has revamped the web series “Ask a…”, a show with the premise of getting to ask questions to someone that you may not interact with on a regular basis. The duo started the weekly series a few years ago, but have worked hard to revamp it and really get into it for the second go-around, and their efforts have resulted in episodes like “Ask a black Trump supporter,” “Ask a former meth head,” and “Ask a Crip,” with a number of episodes ready to follow.


“Kev is a Christian, and a lot of his followers on social media are Christians, so the show originally started out as a way for his followers to interact with someone they would never really interact with, like ‘Ask a Jehovah’s Witness,’ or ‘Ask a gay black man,’” says Hollingsworth. “But we’ve really opened it up since rebooting it. And although we’re two comics doing the show, we don’t do the interviews to try and have any sort of ‘gotchya’ moments. It’s really just us asking questions.”

Another project Hollingsworth is involved with is a pilot production for a series that will, in a way, take his upcoming trip to Massachusetts full circle in terms of his stand-up career. Through interviews with those around him in the comedy scene, and discussions with the big man himself, the story of his stand-up journey will be told, with a lead-up to where he is in his career now.

While he’s excited for the opportunity, Hollingsworth is really hoping that, with this trip back to the area, the luck of the Irish will be on his side when the project makes its way to getting picked up.

“They wanna use me as a pilot, and they plan on doing full seasons of following comics around where they tell their whole story,” he says. “Hopefully it gets picked up, but knowing my luck, it probably won’t.”

BIG IRISH JAY HOLLINGSWORTH :: Friday, March 1 and Saturday, March 2 at WooHaha Comedy Club, 50 Franklin St. in Worcester, MA :: Friday at 7 p.m. and Saturday at 8 p.m. and 9:30 p.m., $20 :: Advance tickets