Jay Gillespie brings musical magic and community spirit to StoopFest

Jay Gillespie and South Boston NDC event planner Jenni McNeill.

When South Boston’s inaugural StoopFest hits the streets, one of the driving forces behind the scenes will be local comedian and music enthusiast Jay Gillespie. Known for his sharp wit and generous spirit, Jay has stepped up in a big way to help South Boston NDC Event Planner Jenni McNeill bring this grassroots musical celebration to life — and he couldn’t be more excited.

“I was honored to be asked to help out,” he said.

The first-ever StoopFest, organized by South Boston NDC and the South Boston Chamber of Commerce, will take place on Saturday, May 31, starting at 1 p.m. This vibrant new music event is designed to bring the South Boston community together while supporting local businesses.

Jay’s journey to becoming the unofficial “cat wrangler” of StoopFest began, as many great community stories do, through a web of local connections. He had known Jenni from her time at Deja Brew. Jay was recently talking with Cathe Walsh of Deja Brew about StoopFest and Cathe mentioned Jay to Jenni. And the rest, as they say, is history.

“Honestly, I couldn’t have done this without Jay,” said Jenni. “Some things we did together were fun and some were not and Jay handled everything with such poise and grace. 

“The fact he took time out of his life to volunteer to help shows what this community is like and how much people are willing to do to help this neighborhood and small businesses.”

Though he's never officially organized a music festival before, Jay’s decades of experience in music and comedy scenes made him a natural fit.  

Jay has spent hours researching the musicians, often “stalking their Instagrams” to get a feel for their sound and energy. He has helped match bands with locations. And he’s doing whatever else he can to help Jenni.

The music vibes range widely — from harpists to metal bands to singer-songwriters — and that’s what makes it great, Jay said. He wants to make sure every act has a spot where they can shine.

Although he’s performed on many stages as a comedian, and has helped musicians in the past, this marks Jay’s first time helping organize a community-wide music event. Still, he feels uniquely prepared as comedy and music have a lot in common — it’s about creating a vibe, making people feel something.

“We’re having a pretty nice turnout for something that hasn't happened before,” Jay said. “All the musicians are wicked excited to come out and play for people.”

Jay noted it’s been kind of rough for musicians and comedians as they face a lack of performance spaces since the pandemic. “So, something like StoopFest is huge.”

 He continued: “I'm thrilled to be a part of it. I'm not even kidding. I love South Boston. It's been my home for over 30 years now. To be able to help get this off the ground, and to culturally add to Southie, is something I’m very happy I was asked to do.”

His love for performance is deeply rooted, growing up watching comedy legends like Richard Pryor and Robin Williams on HBO. While he’s always been funny, he didn’t get the nerve to try stand-up until his 40s, and he’s been doing it full time since the pandemic. He and his comedy partner are looking to start on podcast on mental health. “I think humor is a great way to actually get people to talk about their feelings.”

While he's not sure exactly what his role will be on the day of StoopFest, Jay’s ready to jump in wherever he’s needed. “I'm just looking forward to checking out something new and creative and musical.” 

He believes the neighborhood is ready for something like StoopFest. “Once we break the seal and make it a real thing this year, I think it's really going to take off. There’s a real community feel in South Boston right now.

“Being able to take all this as a learning opportunity in my hometown, and to deal with my passions, it's been an incredible gift … because people, Southie, and music are what make my heart beat. So, to be able to mix all three, it's really good.”

With community champions like Jay Gillespie helping to make it happen, South Boston’s StoopFest is poised to become more than a music event — it’s a celebration of neighborhood, creativity, and connection.