Photo by Jeremy Driesen

I find Mike Benjamin towards the back of his Edgartown property. He’s in his studio, shirtless, and working on The Next Big Thing. It’s the day after the Vineyard Haven Beach Road Concert series, where he and The Mike Benjamin Band has just performed the night before, and I’m honored he’s taking the time to meet with me.

He greets me warmly and enthusiastically, offers me hot coffee, iced water and homemade pickles from the cucumbers he’s grown in the garden, and they’re delicious. Mike has an intense look, with deep, soulful eyes hidden behind his bright-teal-rimmed glasses. His facial hair is neatly trimmed and his salt-and-pepper mane looks like it has been freshly cut. We sit outside in the cool breeze and warm August sun, surrounded by stone fruit trees and floating dragon flies, and start chatting.

Beloved island musician, Mike Benjamin has had an illustrious career, but he describes himself as just being fortunate enough to get paid for doing what he loves to do — play music. Even after studio recording sessions with legends like Patti LaBelle, Paul Shafer, and Marc Cohn, sharing the stage with greats such as Bo Diddly, and Brad Paisley (to name a very few), and even after an impressive success as a session and jingle singer in NYC, Benjamin is still excited that he gets to play.

“It’s always felt a little bit like magic if I played music and someone gave me money, you know? I was like, ‘THAT’S MAGIC!’ Out of nothing, I sang and I played and someone was like, ‘Here’s some money.’ It’s just nice. I just feel like, man, I am cheating the world! I like being able to pull this off, you know?”

Benjamin has been “cheating the world” since he was 13, playing the streets of Cambridge and Harvard Square, though his aptitude for music started when he was much younger. Both of his grandmothers played piano and he took to it right away. With a set of keys at his disposal in the basement, Mike taught himself to play by ear, figuring out how to mimic his favorite television shows’ thematic music, commercials that stuck out in his head and, of course, Beethoven’s 9th Symphony.


Mike Benjamin plays to a lively crowd during the 1st annual Beach Road Weekend concert Photo by Jeremy Driesen

Though gravitating towards the piano in his younger days, Benjamin admits that he was never “particularly good” at it. In spite of that, he still enjoyed playing around with the melodies. “I’ve always enjoyed that aspect of playing,” says Benjamin. “It’s like a puzzle. You hear something and you go, ‘What is that?’ And then it’s a puzzle you try to solve. You try to figure it out. I love that.”

Benjamin goes on to describe a “big moment” at the age of 13, when he got into some trouble and was kicked out of school. “It was two weeks of bummer time.” But instead of giving into the bummer, Benjamin realized that he had a guitar laying around and “just turned the energy towards that and I played.” And that’s when Mike started taking music seriously. “I just dug into it, in a serious way…That moment was definitely pivotal.”

Describing music as a “rescue-focus” in his life, Benjamin reflects that the music chose him — not the other way around. “It was always the thing, somehow. I feel lucky. Again. I feel like I’ve pulled the wool over the system’s eyes. And every year I go, ‘I can’t believe I got people to pay me to play music again this year.’ It’s pretty lucky.”

Mike went on to study musical theory at Hampshire College at the New School in NYC, where he was allowed to create his own program of education for graduation. Like most things in life, he learned more by doing than by studying, but college was never a question in his or his family’s mind. “That’s just what you do, you go to school,” says Benjamin. “But music made the most sense for me.”

Benjamin and his wife came to the Island with the intention of staying through the summer and then heading back to NYC in the fall. But, that’s not exactly the way things turned out. “I did go back and tried to…hustle up some [more jingle] work again, but it really quickly became clear that, like, it’s over, you know? That little scene, it’s over. It’s gone.”

Benjamin headed back to the Vineyard and started picking up gigs in bars and such. During that time, Benjamin says he never advertised to play at parties; it would just happen. People would solicit him to play a party here or a wedding there, and after some time, Benjamin realized there was an opportunity on the island that he wasn’t going to find back in New York. Soon after, he started to put his name out there a little bit more, and The Mike Benjamin Band took formation.

“[It’s not like I] resigned myself to it, more like, okay! Bring it on!” said Benjamin enthusiastically. “It’s the best way to make money. Play music. How cool is that?” From the way Mike tells it, everything about his musical career has just sort of…happened. The band was slowly pieced together, even though he had never held auditions for anyone.


A close up of Mike picking the strings of his guitar on stage at the Beach Road Weekend concert Photo by Jeremy Driesen

After playing gigs all over Martha’s Vineyard, they produced a self-titled album, the Mike Benjamin Band. The songs were inspired from events in Mike’s life. One of his hit songs, “13 Dollar Check” was inspired by Mike’s buddy and fellow musician, Judd Fuller. Mike explains that they were both in NYC in a band together, but Fuller always seemed to be down on his luck for a stretch of time. “He just couldn’t walk down the street without something [bad] happening… He kept getting fired from his jobs, his car would get towed, his girlfriend broke up with him, just ENDLESS,” Benjamin explains.

One day at rehearsal Fuller asked whether anyone was able to cash a check…for thirteen dollars. “And I was like, what are you even doing with a check for $13?? First of all. And then second of all…you need that cashed right now? Like, that’s fucked up!” Benjamin says he gave him $20 and let him keep the check. At the following rehearsal, one of the other bandmates came up with a version of one of the lines in the song but still, it sat there, in the recesses of Mike’s brain. That was 27 years ago. Benjamin estimates that just five or six years ago, he got two residual checks from BMI — both for $13! “And it was $13 check, 113th check, 13th chord, there were 13s all over it.” The song was born.

“There are a lot of players out here that are unsung heroes, flying under the radar. Like I consider myself. I’m not out in the world, doing these giant tours. I’m doing this other thing…I think I’m appreciated. Most of the time.”

Being appreciated and getting paid to play music continues to make the most sense for Mike Benjamin, a man who plans to never retire. He looks to music legend John Fogerty (lead singer, lead guitarist, principal songwriter, and founder of Creedence Clearwater), and reflecting that what he — what Fogerty is doing — is “the ultimate dream.” Touring around with family, playing with his kids…that’s the life Benjamin imagines for himself.

And that fantasy isn’t too far removed from reality. Currently, Benjamin’s daughter is off in London, having recently signed her own deal with Moshi Moshi Records. Benjamin’s son plays bass and has his own band, Slammy B and the Electric Snakes, though he still sits in with dad Thursday nights at The Ritz. Benjamin beams when talking about his kids and their success. “When [my daughter, Charlotte] is stuck, she’ll come in with questions… And I LOVE to be able to sit down and show her some chords or something. My son, too. It’s a blast to be able to sit down and teach him some stuff.”

All smiles and good conversation with daughter Charlotte and guests at dinner. Photo by Jeremy Driesen

Today, Mike and his band can be found playing gigs all around the island. You can catch his set Thursday nights at The Ritz in Oak Bluffs.
Mike Benjamin’s current band is made up of moving parts. But the consistent players include:
Mike Benjamin, guitar/vocalist
Wes Nagy, keyboard
Steve Tully, sax
Scott Schettler, sax
Sophie Hiller, singer
Joanne Cassidy, singer
Darby Patterson, singer
Brad Tucker, bass
Robbie Soltz, drums

*Mike Benjamin makes a special note that Joanne Cassidy and Darby Patterson are his “dream backup vocalists” and would have them on with him at every, single gig, if not for their commitment to their own bands.
You can book the Mike Benjamin Band through the band’s website
Instagram: @thekeepersmv
Facebook: @mikebenjaminband