Marblehead Native Michael Regilio Shifts from Music to Comedy with Debut Special “War Bar”

Michael Regilio, a Marblehead High School Class of 1990 graduate, has made a bold leap from indie-rock musician to stand-up comedian — and he’s already making waves with his first comedy special, “War Bar.”

Born and raised in Marblehead, Massachusetts, Regilio began his creative journey playing in a high school band called Jane Road. By 27, he had relocated to Los Angeles, chasing a career in music. Over the years, he recorded several indie-rock albums, balancing his artistic ambitions with day jobs to stay afloat.

But at age 44, after nearly two decades in music, Regilio decided it was time for something new. “Music just didn’t quite have the sparkle it used to have,” he explained. “I’d always loved comedy — I’d always been the class clown.”

That love for humor got a push from his good friend Alex Ouanes, who surprised him by paying for a stand-up comedy class. Initially hesitant, Regilio only agreed to go when he learned Alex had enrolled himself too. “We took the class together,” Regilio recalled. “After two hours, they told us to write one minute of stand-up. I got up with that one minute, got my first laughs, and I was 100% hooked.”

Ten years later, that impulsive moment led to something major: Regilio signed with Comedy Dynamics, one of the biggest comedy labels in the world. His debut special “War Bar”, released October 7, 2025, is now streaming on Amazon Prime Video, Apple TV, Google Play, Vimeo, and YouTube.

The half-hour special was produced by Jack Vaughn, a four-time Grammy Award winner known for working with Jim Gaffigan, Dane Cook, Joe Rogan, Maria Bamford, and others. Described by Comedy Dynamics as “razor-sharp wit and infectious energy,” the special features Regilio’s distinctive mix of political and cultural commentary — and his fearless sense of humor.

Regilio says one of the highlights of his comedy journey so far was performing at Upright Citizens Brigade (UCB) in Los Angeles, a venue famous for launching comedic talent. “To get on stage in front of a loving audience — I was lucky enough to do it there,” he said.

True to his roots, Regilio brings a lot of Marblehead to his comedy. He often references his teenage years, including nights spent swimming at Crocker Park with friends. His hometown even inspired his latest screenplay, “Young Republicans,” a story based on the time the Marblehead High School Republican Club took a chaperone-less trip to Washington, D.C. for George Bush’s inauguration.

Beyond stand-up, Regilio runs a podcast called “Regilio vs. Everything,” where he dives into current events with a mix of humor and outrage. “Someone emailed me and said, ‘I was a happy person until I found your podcast — now I’m fuming mad at the world,’” Regilio joked. “I said, ‘Good. You should be. There’s no point in being happy right now. Be mad and do something about it.’”

Looking ahead, Regilio hopes to expand his platform. “In five to ten years, I’d love to have a daily outlet for my political and comedic rants — ideally through my podcast. But if HBO wants to hand me Bill Maher’s show, I’ll happily take it,” he quipped.

Regilio now joins a growing list of Marbleheaders who’ve made their mark in comedy, alongside names like Rob Delaney (MHS Class of 1995), and stars Seth Meyers and John Mulaney, both of whom have family ties to Marblehead.

You can follow Michael Regilio on Instagram (@michaelregilio) to keep up with his latest projects.