MARTHA'S VINEYARD, Massachusetts — In an industry in which bigger is better and money is the bottom line, singer/songwriter Willy Mason has managed to fashion a career without playing by anyone's rules. Discovered at 16 on a radio station in his hometown of Martha's Vineyard, Mason has seen his songs scale the charts in the U.K. and has taken his show on the road with acts like Radiohead and Death Cab for Cutie.
The singer recently returned to the island — a summer hot spot for the rich and preppy that seems an odd match for a rough-and-tumble folkie — to play a benefit show at Outerland for WVVY, the station that gave him his big break. You wouldn't have noticed Mason before the show, as he stood near the back of the island's sole nightclub chatting up friends — dressed in tan carpenter pants and a loose cotton shirt, it was difficult to tell him apart from the hordes of twentysomethings in the audience.
As soon as he took the stage, however, it was very clear that he was the star. People sang every word to songs from his latest album, If the Ocean Gets Rough, cheered loudly and demanded two encores.
When it was all over, Mason left the audience sweat-drenched and crying for more. But instead, he went off into the quiet night, leaving the locals to spill out into the Vineyard, off to beach parties and elsewhere. As for Mason, the singer barely finds enough time to unwind, even during his brief respite at home.
"I like the beach, but just sitting there for a long time or hanging out makes me feel like I'm wasting time," he said. "I always think about the stuff I should be doing. It stresses me out. I know it's f---ed-up. I'm trying to relax a bit now, take out the trash, fix the porch."
Quotes like that don't make it readily apparent, but it's his laid-back style — coupled with his lyrics, of course — that makes Mason both approachable and accessible: He can play a sold-out concert hall one night and hang out in someone's garage the next. He bridges the gap between artist and fan, admitting that, for the most part, he enjoys the small shows that allow him to interact with his audience and have a "musical conversation."
"In Amsterdam, I'd sing a song, and then we'd just end up talking about what I was singing about for a long time," Mason said. "[The song] 'We Can Be Strong,' for example — I figured it was maybe just a small-town thing, kids dropping out of school and kind of depressed about being here. But they had the same feelings in [places like] Israel and the same problems, and so everybody was kind of talking about it, realizing, 'Yeah, it's just like where I live.' "
Mason hopes to continue spreading his message on an upcoming European trek, plus a couple of support slots on "big tours" scheduled for later this year (his publicist wouldn't confirm just who he'll be supporting). But what will happen after those tours are done and he finds himself back on the Vineyard?
Mason's not quite sure. And that's just fine with him.
"I feel like I've definitely gotten used to just doing my thing, I guess, and now I'm trying to figure out what the next move to make is," he said. "I imagine it's a similar feeling to being in college. I'm working hard and learning a lot and making a lot of connections, but my mind is always towards the next thing. What's gonna happen when I graduate?"