Mike Benjamin: Don’t miss this Island troubadour

Mike Benjamin shreds with his band at the Harbor View party last New Year's Eve. —Sam Moore

By M.A. Kent-Holmes 

Mike Benjamin has been playing music on Martha’s Vineyard since he was an ambitious teenager nearly 40 years ago, and he’s still going strong, playing in multiple bands year-round, and working on solo writing and recording projects.

Benjamin, who grew up in Cambridge, “fooled around” on the piano as a small child, he says, and started playing guitar and “got more serious about it” when he was about 12.

“I used to play in the streets in Harvard Square with friends and stuff, and [played] in the subways in Boston, busking,” Benjamin said in an interview with The Times at his home recording studio in Edgartown. Mike and a friend, Willy Haigh, came to the Vineyard in 1980, the summer after Mike’s junior year in high school.

“We were like 16 or 17,” Mike says. “Basically, our mission was … we’re gonna get a gig somewhere.” They found a place to live, in the attic of the historic Corbin-Norton House on Ocean Park in Oak Bluffs. He recalls that before the house burned down in 2001 and was later renovated, it was “a giant, crazy, messed-up Victorian.”

The duo’s first gig was at a place called the Coffee Shop, in the building that now houses Sharky’s in Oak Bluffs. “We had a little gig there in the window, and that was a big deal,” Benjamin says. “That kind of charged us up, so the next summer we came back with a band.”

The band, Kitch ’n’ Sync, lucked into regular gigs at the legendary Seaview, owned by Loretta Balla and frequented by a colorful cast of characters, most notably Oliver Perry, known to most as Johnny Seaview. Mike and friends had dropped off a press kit with a glossy 8- x 10-inch photo at the Seaview and other venues earlier in the summer, but their calendar was still empty when he got a call from Loretta saying, “You kids are playing here tonight.” The original entertainment had canceled, which worked out well for the band of supposed 18-year-olds (some were, some weren’t).

“We played the Seaview,” recalls Benjamin, “that was our little venue. Then from that, we picked up a bunch of parties. It was just a blast, and I always remembered it.”

After that summer, Mike went to college in New York City, but he returned to the Island periodically every summer. “Maybe for a week or two, or half a dozen weekends, I’d come up,” he says. Sometimes, he recalls, “I’d come up for the weekend and I’d stay for three weeks [because] I’d end up playing some gigs.”

When he was in his early thirties, Benjamin bought the house he still lives in, and moved to the Vineyard full-time. “I was doing studio work in New York, playing in bands, playing in the bar scene,” he recalls, “then I got into this whole recording scene, singing people’s song demos, and singing radio and television commercials. I saved some dough, and in ’94 [I] bought this place.” He wasn’t sure he could afford it at the time, but says now, “Here I am, 25 years later.”

Since then, Benjamin has cut multiple albums of his own, and played on probably a dozen albums for others, along with playing live gigs year-round. He’s also done the recording for two of his own albums, and several by others, including one by Johnny Hoy.

Although nearly four decades have passed since that first summer, Benjamin’s energy and passion for music don’t appear to have slowed down. He heads the Mike Benjamin Band, which plays at the Ritz year-round and at the Port Hunter in the summer. He also plays in the Grateful Dread, a reggae-style Dead cover band that packs the Port Hunter in the summer; and he plays about a dozen weddings a year, as well as other private parties. He occasionally still plays with his former band, Entrain, although the band is now fronted by Brian Alex.

“The thing I appreciate most about Mike Benjamin is his versatility,” says Brice Contessa, manager of the Port Hunter in Edgartown. “Stylistically, he’s incredibly adaptable.” At a Mike Benjamin show, Contessa says, “you might hear a Duke Ellington tune followed by an Allman Brothers song and then an Amy Winehouse number, and they can play literally everything in between. From funk to rock, soul to country, pop to jazz; watching the band seamlessly transition between genres is truly a sight to behold.”

On Thursday nights at the Ritz, Benjamin represents the Edgartown part of the Edbury All Stars, which Contessa describes as “a rotating ‘dream team’ of local artists anchored by Mike and Johnny Hoy.” Edbury’s other core members are local heavy hitters Jesse Leaman, Kevin Medeiros, and Willy Mason.

“It’s kind of an inclusive jam,” Benjamin says of the All Stars, who play year-round. “We play a bunch, and then we just get the people who are there to sit in.” Featured sit-ins include Brad Tucker, Bluefish guitarist Delanie Pickering, Rose Guerin, and many others. “It’s not an open mic night,” Benjamin says, “it’s a local sit-in night.”

Benjamin is looking forward to these and other gigs this summer, including a possible trio or four-piece at the Eisenhower Gallery, and solo or duo spots at new restaurants the Town, at the former Grille location in Edgartown, and the new hot spot coming soon at the former Lola’s in Oak Bluffs.  

As always, he’s working on developing and recording his own original songs as well. “I’m in the middle of a project now,” he says. “Last spring I started a bunch of new tunes, and I’m just trying to finish them all, and I’m getting there.”

“Whether it’s a capacity crowd for Grateful Dread on a summer night at the Port Hunter,” says Brice Contessa, “[or] a funky February Thursday with the Edbury All Stars … you can be sure of one thing — [Mike’s] legions of fans from the Island and beyond will be shaking their hips and hanging on every note.”