Entering Willy Mason’s West Tisbury home is a little like visiting an archeological dig into his ancestry. A haphazard collection of reclaimed family history fills every available space. Which is apt, really. The house is like a physical metaphor for his music, which also is rustic, familiar, and encrusted with bits and pieces gleaned and saved up from several generations of forebears.

The twenty-two-year-old singer-songwriter makes half-hearted apologies for the mess as he makes his way from the porch storage area into the front door of the snug, shingled cottage. “I’m gonna have a party here,” he says optimistically, “once I can get people in the door.”

He soft-shoes a path to an old sofa covered with mismatched throws, past ceiling-high stacks of shelves crammed with oversized dictionaries, Don DeLillo novels, books about pioneer women and anthologies of poetry, work by Philip Roth and about Chuck Berry. There are coffee table–art books from Willy’s paternal grandfather’s ground-breaking publishing house, and books written by Willy’s maternal great-great-grandfather the philosopher William James, and great-great-grand-uncle novelist Henry James.

A picture of great-great grandpa is framed with one of his letters and hangs near the baby grand that belonged to grandma. On the same wall is a signed Picasso drawing of Willy’s grandfather, who published The Private Lives of Picasso – actually, it’s a scan, since the family decided to sell the original. Art by Willy (a childhood collage in felt and burlap titled “My Dad Love Willy”), and by his mother and younger brother Sam hangs there too.

Before he can reach the sofa, Willy’s black suede skateboard sneakers have to sidestep the precariously balancing piles of vinyl, cassettes, and compact discs, some recorded by his mom and dad, others by Island musicians of his and his parents’ generation, still others from little-known bands Sam scouts out on the Internet. There’s Glenn Gould, Van Morrison, and Little Feat, sitting beside homemade cassettes.

Artfully dodging guitars that everyone in the family plays, when the instruments are not hanging between the books, Willy warns not to trip over half a dozen speakers set up in front of it all. He skirts around the old Hammond organ Sam found at a thrift shop, grabs an ashtray, and edges the dining table that holds not china but electronic equipment, from which Sam is coaxing soft, otherworldly rhythms. Sam nods hello and continues to tinker, providing a rhythm track to his brother’s interview, as he does for his recordings.

The boys’ mother, the accomplished songwriter and performer Jemima James (who has long been called Mimy), offers herbal tea and asks when his father, songwriter and musician Michael Mason, will be back – or even where he is. Nobody is sure.

That Willy Mason is enmeshed in his Island history is evident in the house he bought for his family last year. He bought it from them too; the whole place once belonged to his grandmother, who, when she died in 2002, left it to Willy’s father and aunt and an uncertain future.

Last summer, Willy’s dad gave his half to his son, so that Willy and the bank could buy his aunt’s half. He bought it with the earnings from his first major record contract, a three-album deal with Virgin Records in the United Kingdom.

A platinum-selling artist in England at twenty-one, Willy wrote what became his first hit single, Oxygen, for his Martha’s Vineyard Regional High School music theory class. He’s been called “Bob Dylan for The O.C. generation” and compared to Johnny Cash and Bruce Springsteen. When pressed, Willy has described his sound as “a kind of bridge between my mother’s John Lee Hooker and my father’s Hank Williams.”

“It goes back farther than Mimy and me, though,” nods Willy’s dad, who has shambled back in and joined the conversation.

Just now, family history is threatening to overwhelm Willy Mason. He’s trying to play a track from his freshly pressed compact disc, called If the Ocean Gets Rough. But so tangled are the stereo wires that weave among his family’s myriad musical equipment, recordings, books, and random keepsakes, it takes his father several minutes and sheepish apologies before strains of the new tune Riptide finally begin to play.

Out of the speakers comes a spare song line. It’s just Willy at first – languid, sounding lonely, a cappella – I need a new song, twisted all around, like the ocean, when the riptide gets you down. Gradually a groove, set by Sam on drums, swells around Willy’s acoustic guitar. And Willy’s voice, much richer than his age might suggest, stretches each word: Take some, from the ones you love, in the old town, when the riptide gets you down . . .

This is Willy Mason’s old town. It’s what he knew before he got caught in the riptide of becoming a music sensation on a major music label; before he was the opening act for performers as diverse as Radiohead, Roseanne Cash, Beth Orton, and Death Cab for Cutie; before he started drawing rapturous bar-hoppers together with their parents for his packed-out solo gigs across England; and before his long, isolated stretches on tour and on borrowed sofas, making a living out of making music, all somewhat by accident.

Here is where he makes sense of it. Willy drags on an American Spirit cigarette (no additives), while his spare, soulful single fades from the speakers. The lyrics, he says, were inspired by his life on the Island. The final lines?

I guess you could say that this is me. And I guess that these folks are the only ones I believe.

Willy Mason is home now, surrounded by the ones he loves. With all of them here, this comfortably chaotic house, like many of his songs, has a perfect internal logic. Martha’s Vineyard is where young Willy learned to play cello, drums, bass, piano, and guitar. Here he learned to play all the characters in Billy Balloo, the stage musical his parents wrote together. It’s where Willy wrote his first song, after seeing a largely forgotten band called Cavity Search at the late, lamented Wintertide Coffeehouse in Vineyard Haven.

“I was like ten or eleven,” he recalls. “I went home and wrote a song, pretty much.” Was it any good? “No.” Do you remember it still? “Not really.”

In this very same house, Willy’s first band rehearsed. “It got pretty loud when I was in grade school,” he shrugs of his Black Sabbath–style starter outfit. “For a while, we started actually practicing here in the basement, because my grandma’s hearing was starting to go a little bit.”

This house is also home to Willy’s nascent Internet retail music business, appropriately called Grandma’s Basement. When she died in 2002, the obituary in the Vineyard Gazette invited friends to bring an instrument and join the family for a musical celebration of her life at Abel’s Hill Cemetery.

Rees Mason was a trained dancer, pianist, and singer; her husband Jerry was a journalist and music lover who founded the Ridge Press, one of America’s first independent book-production firms. On the Vineyard, where they summered, they were the center of a thriving up-Island music scene. So many people gathered for their weekly singing and guitar playing, Rees’s “sings” eventually outgrew her living room. Thanks to that, she helped create the Chilmark Community Center.

So it was that Willy’s parents, both musicians, moved to Chilmark when Willy was about five years old. His mother, Jemima, sets down the tea and explains, gently. “Mike’s parents lived here in the summers, and then they retired here to Chilmark – Stonewall Beach,” she says. “And we moved up in ’92 – when Mike’s father died and his mother was alone – from Tarrytown, New York.”

Willy went to the Chilmark School. “Graduated from there,” he says proudly. “Stayed with my grandma for a while, and then we shifted around.”

Jemima says they “did the Vineyard move thing.” Shacked up cheap in summer, something better for less money in winter. Even moved a baby grand sometimes. “It’s hard on your children,” she says.

Willy deadpans, “Just keep losing stuff, and it becomes easy.”

He laughs, but he also is dedicating money from his own musical success to support affordable housing on Martha’s Vineyard. Rees sold the Stonewall Beach place after her husband died, but before it realized anything like its value these days. She later bought the house in which we now sit.

Times were hard, says Mike. “We were broker than you can imagine. I was working for twelve bucks an hour at various times. It was financially really hard for the boys, and I think that’s reflected in Willy’s music.”    

“We did what we could,” says Jemima, who grew up in Colorado. Her long literary and artistic lineage began with William and Henry James, and her father was a portrait painter and talented guitarist and banjo player who sang a lot of Huddie “Leadbelly” Led- better and bluegrass when nobody else was listening to that. By the ’70s, she was a staff songwriter for a music company in New York City, performing in clubs on both coasts, and she has recorded albums on and off since then. She first invited Willy to join her on stage when he was thirteen.

Mike Mason worked with Jemima writing songs on the forty-first floor of a New York City skyscraper. He also signed with Columbia Records, but then, as Willy has told the story, “he got into a fight with his boss and punched him out, so the album didn’t come out.” The way Mike tells it, he was the one that got punched – okay, he did call the guy a punk – but either way, Mike pursued his songwriting and performing independently after that. He still does.

Tonight Jemima is visiting, for a week or so, up from Durham, North Carolina, where she has lived since she moved out last year. Mike still lives here year-round, sending out shipments every few weeks from the Basement, which is less a fully realized business than a few shelves stacked with CDs in the even-more-cluttered downstairs. Sam was enrolled at music school in Chicago, but he’s temporarily abandoned studies to tour with Willy.

They all move about the place with warmth and ease, pleasantly and frequently interrupted by a passing parade of drop-in visitors of all generations. It’s how they’ve always been. Wherever they were on the Island, Willy recalls, Jemima and Mike had company. “They used to have a lot of parties back in the day, where everybody would play songs and stuff, and then I started doing my own thing as I got older, and they were always very supportive of that,” he says.    

His dad picks up. “Oh, even back in ’52, ’53, ’54, every summer once a week there would be gatherings at somebody’s house, and there were a lot of musicians up-Island, and a lot of year-round musicians, especially in West Tisbury. Kind of old-timey and early country music and stuff. There were a lot of folk singers.”

Then, he continues, “one summer, when a lot of the get-togethers were at our house, it would spill out into the front yard – there’d be more than one hundred people. James Taylor was playing, he was a bit younger than I was.”

Mike discounts his own noted banjo playing. Plays some guitar, some keyboards. “Songwriter too,” Willy chimes in. “He writes a lot of songs. I play a song that he wrote with my mom, called Way to the Station, and it’s been released.”

Here’s how Willy describes making his own songs: “It’s a complicated process. This house is turning into an assembly line. I steal the melodies from my mom, I write my own lyrics, Dad edits the lyrics, and then Sam makes them sound good.”

Jemima hastens to add, “But it’s not like we’re the von Trapp family. From the beginning, both [Willy and Sam, who is writing his own songs now too] had an innate sense and talent with music. And the best part is, they’ve been able to follow their own taste and ideas about it. . . . They’re very good at being individuals and being true to themselves, and to me that is the most important thing for a creative artist.”

Through the years, both Jemima and Mike have struggled with how to handle the business end of the music industry. So far, it’s been different for their sons. “They learned from our mistakes and in a really productive way,” Jemima says. “I’m very proud of them – very proud of their maturity and way of handling stuff.”

Last year, The Boston Globe wrote a story in which Willy admitted his father fretted about his son’s sudden stardom, and the damage it might do to his spirit and music. “My dad was worried about what any kind of artistic industry can do to a creative mind,” Willy told the paper. “He thought I had a lot more growing up to do before I went to face the music dragon.”

He’s facing the dragon just fine, his dad says with a laugh.

“I accidentally didn’t end up going to college,” Willy mentions. So Mike has started “assigning” his son books to read. Next up is Cannibals and Kings: The Origins of Cultures by anthropologist Marvin Harris, who founded the school known as cultural materialism.

“Which is pretty cool to read as I’m driving across the country,” Willy says with genuine enthusiasm, though his deep speaking voice also is languid, almost shy.

While Willy is on tour, Mike Mason is creating rustic web videos for his son’s MySpace page and minding the Basement. When Willy’s or his parents’ or his friends’ records sell through the Grandma’s Basement website (http://grandmas-basement.com), Mike makes sure $1 for each is donated to the Island Affordable Housing Fund.

“We didn’t have a place to live here, and for a long time, it was looking like we weren’t going to be able to keep this house,” Willy says. “Then, right then, I got a record deal. So it was like, all right, we gotta buy the house. We did.”

Being home grounds Willy. Perhaps it’s because he is suspended between disjointed worlds – being on the road, always somewhere unfamiliar, and being home; being adored by crowds of strangers, then being alone at the bar after the show; being the hottest name in one place and an unknown in the next.
How exactly did he get here? A few years ago, Island photographer Peter Simon wanted to include one of Willy’s songs on an album he was producing for another local singer.

“So in his living room,” explains Willy, “Peter recorded me singing a demo,” for the other guy to learn. “And then Peter played [Willy’s demo] on the radio, on WMVY on his Sunday night show, and somebody from New York was driving on the Cape and heard it.” That somebody was Sean Foley – associate of musician Conor Oberst, who performs in the band Bright Eyes and is known in the industry as a co-founder and executive partner in the independent record label Team Love. “And that’s how I played my first gig in New York, and that’s how I met my manager, and so on and so forth.”

Willy sold his first five-track EP at live appearances and on the Internet. His 2004 album Where the Humans Eat (the title song written about his cats) is raw, driving, and low-fi; it was recorded mostly live – no more than three takes – with Sam, who was then fifteen.

In 2004, when Willy played at the biggest talent-spotting music festival in the United States, Austin’s South by Southwest, there were fewer than a dozen people in the bar. But four of them happened to be DJs on BBC Radio 1. Willy Mason was suddenly the new troubadour of British music. His record sold more than 100,000 copies there. Five thousand people sang along with him at his 2005 Glastonbury Festival gig.

Virgin Records snapped him up. For his new album, If the Ocean Gets Rough, Willy, most of his family, and many of his friends recorded at the legendary Long View Farm studios in North Brookfield, Massachusetts. It’s where Jemima worked as “house mother and cook” in the ’70s. “The Rolling Stones, Pat Metheny, Arlo [Guthrie] came there a lot,” she says. This time around, she still was doing some cooking, but mostly she was adding backup harmonies. Casual as the recording was, this album makes Willy feel like he’s getting serious about the music business.

“With the first record, there really was never a point when I made the decision to go into the music business,” he shrugs. “It was just sort of a string of events that I went along with more out of curiosity than anything else. There was a lot of that kind of serendipity going on.”

But that attitude made his life more difficult.

“Because I never committed to it as a job or anything like that, and so it made it harder to get through the rough spots and the boring spots,” he says. “There were a lot of points where I wasn’t learning anything, and it wasn’t interesting.”

So Willy took a year off before recording at Long View. “And now I’ve really decided to go back into it,” he says.

But with his own twists. “The cool thing with the music business is how open-ended it is,” he muses. “You can bring so many things into it. You can bring art into it, or sort of analytical thought and discussion, and acting. You know, I just shot a music video, and I got to be on a set in front of a camera, and I used to act a lot back in school, so it was like something I haven’t done for a while, and that was pretty cool.”

Changing the way he tours is a new priority. “The way it is set up right now, particularly when I’m by myself – it’s very isolated and boring. Typically, you’re playing a show every night to keep the costs down. So you end up just kinda driving most of the day, show up, play a gig, go to bed, drive all day, and you know . . . any kind of interaction tends to happen after the show, and maybe it’s just hard to break the ice in that sort of situation.”

Don’t fans come up to talk to you? “If they do, they are sort of mystified in a weird way. So it’s very fast-paced and just hard-living in general. But slowly, step by step, I’m making small moves to change that. Because I know the potential is there for it to be a very positive experience.”

The most radical of these moves was to send out a mass e-mail saying that if you had a living room, he’d play a concert there. Free Willy. The first time he did it, last fall, it was just an idea for a road trip he wanted to take anyway. But it’s taking off, and becoming part of a strategy to help him capitalize on his fame while staying focused on what he likes best – the way music can bring people together, across a living room.

“We pulled it off and had a good time, and now I know that it can be done pretty easily and successfully,” he said about the initial round of house parties. “It wasn’t very planned out, but they would just invite their friends over, and I really didn’t charge anything. I would ask for donations. Sometimes we made some money, sometimes we didn’t.

“To do it as a sustainable thing, I’d have to work out some kind of fee, maybe just charge at the door or something. I wouldn’t want people to lose money on it. But you know, usually we got free places to stay, usually just crash on the floor.”

So another mass e-mail went out before Willy began his United Kingdom tour in February, for the album released in March. Requests came in from nine hundred people with living rooms, from Galway to Israel. Willy writes on his MySpace blog of the dozen house-party stops, scattered across the country: “Those familiar with a map of Britain will see my tour routing skills need work.”

But he’s planning to do more during his U.S. tour. The big shows are good, he says, but you give so much as a performer, and it’s hard to see what you’re getting back with all those lights, those people so far away. Not like sitting on their sofas, singing right to them. Willy compares the house parties to his parents’ parties during his childhood, where he played music with his family and their friends. “Those were the best times of my life,” he says.

Back home, Mike is trying to organize all the heirlooms and the junk because Willy, Sam, Jemima, and a Virgin UK crew are coming to film a second video, from the new album, here – at home, with friends and music all around, where Willy Mason likes it best. “That’s just me.”