Up until two years ago, Willy Mason had never played a gig off-Island.

Last week, the 20-year-old singer and songwriter from West Tisbury headlined sold-out shows in Tokyo and Osaka, Japan. A couple months before that, he stepped onto stages in England where Virgin Records has already signed him to a record deal.

"Yeah, it's been a crazy year," Mr. Mason says with a sheepish smile while sitting on a couch in his Mom's West Tisbury home. "Sometimes I can't believe how it's turned out."

In the past year, he's gone from playing open-mikes in small bars to opening up for college radio favorites like Ben Kweller, Death Cab for Cutie, the Cowboy Junkies and My Morning Jacket at large festivals.

CMJ, a magazine devoted to exposing new music, recently featured him in its "On the Verge" section, and the British publication Dazed and Confused called him America's best new songwriter. He has been compared to everyone from Elliot Smith to Bob Dylan, and his shows are discussed on Web sites from fans all over the world.

With the release of his debut full-length album - Where the Humans Eat - you have the sense that this young musician's star is about to take off. The album, a collection of his first EP and several new songs, was released last month.

His career has taken so many twists and turns in the past two years that it is hard to pinpoint when and where he leapt from obscure teenage singer to one hyped in publications around the world. But this unlikely odyssey does have a definite starting point.

One night in 2003, family friend and WMVY disc jockey Peter Simon, played Oxygen, a song Mr. Mason recorded at Mr. Simon's house.

It just happens that Sean Foley, a New Yorker vacationing on Cape Cod, was listening that night and heard the song.

"He loved it, and asked me if I had any other songs," Willy Mason recalls.

Mr. Foley was one of those fans who can make things happen: He worked at Irving Plaza, one of New York's biggest clubs.

"Before I knew it, he was booking me a gig in New York," Mr. Mason says, shaking his head at the serendipity. "It was the one time Peter played it. I was just some senior in high school."

The Foley connection also paid off when he was introduced to Conor Oberst, a musician known over the airwaves as Bright Eyes. It happened at a Conor Oberst show in Northampton. Mr. Oberst had gotten a copy of Oxygen, and was taken by it.

"His writing is lot like mine," Mr. Mason says.

That night, Mr. Oberst called out to Mr. Mason and brought him on stage and played the song to a packed house.

"It was the first time I had ever played away from the Vineyard, and it changed the way I looked at everything," he says.

The next morning, he woke up on the Bright Eyes tour bus in Vermont.

"I was pretty down on where I was in school, and felt all these failures and pressures building up. But then I realized that they had all created these positives. It gave me confidence I never had," he says.

His friendship with Mr. Oberst began to open doors, both professionally and socially.

After graduation from the Vineyard regional high school, Mr. Mason moved to New York, hired a manager and signed with Mr. Oberst's record label, Team Love.

He crashed on couches, wandered the city streets and wrote songs from fire escapes. He toured with the Other Ones, the remaining members of the Grateful Dead, and played at various festivals around the country.

Last March, Mr. Mason got another big break, playing at the South by Southwest festival in Austin, Tex., one of the country's most prestigious and successful showcases for new popular music.

"It was funny because my slot was early in the evening on the first day of the festival - the worst time to get," he recalls. "There were about three people in the bar paying attention to me and maybe four at the bar drinking."

But after his set, those three people approached him.

"They had British accents, and asked me if I wanted to play some more of my music for them."

They turned out to be disc jockeys for BBC 1 radio, and asked Mr. Mason if they could feature him on one of their broadcasts. He played several tunes sandwiched around an interview, and only days later, the calls came flooding in.

"England responded so quickly," he says.

Within days, a representative from Virgin Records in London contacted him about a potential record deal, which he signed a few months later.

He is currently signed on three separate record labels in three different continents, including another in Japan with Bad News Records.

A six-week tour in England ended in October. He will return to Britain in February for another month-long tour this time as the headlining act.

His new album was recorded earlier this year over 10 days of studio sessions in a house in Catskill, N.Y. The 12 songs - the Japanese import has 13 - range from quiet and contemplative folk to twangy country and blues to all-out romping rock 'n roll. His influences are obvious. His mother, Jemima James, is a well-known Island folk singer and songwriter. His father, Michael Mason, is also an accomplished musician. His younger brother Sam, a senior at the high school, plays drums on the album and frequently backs him onstage.

Mr. Mason grew up playing guitar, but his most impressive talent is his own songwriting. His songs are acutely perceptive and reflect a life lived almost in another time and in another place. In the best folk and blues traditions, he sings of hopelessness in alleys, single shots ringing out in the streets and selling souls to demons at the bottom of a hill.

Yet he also conveys a real-life angst that speaks directly to the anxiety of youth in today's America. Oxygen is a prime example, expressing a yearning to break through and free to a world more real, more responsible.

"I wanna be better than oxygen, so you can breathe when you're drowning and weak in the knees," he sings. "I wanna speak louder than Ritalin, for all the children who think that they've got a disease. I wanna be cooler than TV, for all the kids that are wondering what they're going to be."

"Do you remember the forgotten America?" he continues. "Justice, equality, freedom to every race. Just need to get past all the lies and hypocrisy, make-up and hair to the truth behind every face. Then look around to all the people you see - how many of them are happy and free?"

Through his association with Bright Eyes and his numerous tours, that one cut has become an underground anthem, spreading across the airwaves of college radio stations around the country.

"Every song has a story, mostly of heartbreak," Laura Simmons of BBC 1 wrote after seeing one of Mr. Mason's shows in London. "Willy introduces them with a little bit of explanation of what they are about each time, which makes the gig seem sort of intimate, you end up feeling you know this guy inside out."

Back on the Island this week, on a rainy night at his Mom's house, that intimacy is amplified as he picks up his guitar to play a tune with his family at his side.

He plucks the first few chords of Fear No Pain, a rollicking song about the emergence of confidence and hope. He sings a few lines as his brother starts to pound away on the bass drum, and soon Mom starts in with the harmony. Dad starts strumming along on another acoustic guitar.

"I'm gonna be leavin', I'm gonna be leavin' soon this I know," he croons. "I'm gonna be leavin' soon where the water tastes like moonshine, I'm gonna be leavin' soon this I know."

His words are prophetic. Soon he will depart the Vineyard for more shows, spending more time away from the Island, almost certain to attract more fame.

"People talk about keeping fame or popularity in perspective, and that, for me, is really important," he says. "But honestly, I don't really think about it." Looking around the room, he smiles.

"This makes it all normal."

Willy Mason plays two shows next week: Thursday at 7 p.m. with Elisha Wiesner at Above Ground Records in Edgartown, and Friday, Dec. 17 at 9 p.m. at Offshore Ale in Oak Bluffs.