You spend your life, from age six, learning to play music. You go to the New England Conservatory of Music and spend more years mastering theory, harmony, writing.

Then you live an itinerant, gigging life for a few years before going to New York, doing session work with some big stars, and making good money writing ad jingles for Levi’s, Ford, Pepsi.

And one day, you find yourself closing in on forty, no longer doing jingles for Pepsi or Levi’s, but for Depends and Pampers.

It was time for Jerry Bennett to take stock of his life. “I thought: ‘I’ve got to get the hell out of here,’” he says.

Where he got out to was Martha’s Vineyard – more specifically to the old Sea View Hotel in Oak Bluffs, where he began playing the odd gig with a friend. “There used to be a bar down there where people would literally be barefoot,” he recalls fondly. “They’d walk out on the beach and smoke pot. It was like Hippieville. It was so un-New York. And I kept coming up. For two weeks, then a month.”

Then it dawned on him: Fun as it was, the Vineyard music scene was less sophisticated than the Vineyard itself. There was blues and rock and roll, but there was no “event” music. “I thought, There are wealthy people here, and I know what they expect. All the while I was in New York, I would play here and there. I knew what the ‘event’ of music required, and there was nobody doing it here. And I had a built-in network of people I knew from the conservatory alumni and all the people I met in New York. The best singers, the best musicians in the world do jingles,” he says. So, in 1996, Jerry Bennett’s Sultans of Swing was born, with him on drums and various members of that large network filling out the band.

“We started doing weddings and my first singer was Susan Tedeschi – who later won a Grammy – and Mark Grandfield, who still works with me,” says Jerry.

Ten years later, the Sultans of Swing is a virtual franchise, with clones of the band – ranging from six or seven to fourteen members – often playing simultaneously in different parts of the country. Collectively, they will play close to 200 events this year, although Jerry himself will play only about one-third of them. “On a busy weekend, we’ll have fifty musicians playing, anywhere from Maine to New York City, all working as the Sultans of Swing,” he says. “We have a growing business in south Florida, in Palm Beach, and now Sarasota. It’s an orchestra in the mold of the classical, event orchestra, like Lester Lannin had, where there would be four or five Lester Lannin orchestras out following the same song list, with the same approach.”

Bennett lives in Edgartown, and dealing with the logistics now is too much for one man – the company has a business manager, who coordinates with the clientele on repertoire, and a musical director, who downloads the music, prepares the charts for all the musicians, and sends them out to the various band leaders. There also is a password website where the musicians can download MP3s of the songs they have to learn. Jerry Bennett even runs a second house on the Island as a band house.

But complicated as the business has become, the secret of the venture’s success, he says, is pretty simple. “It’s knowing what’s going to get people to dance, loving all different types of music, and having musicians good enough to play it all. In a given set we’ll play Beyoncé, Nat King Cole, some country, Frank Sinatra, AC/DC. Other bands just don’t have the ability to do that – to play in a variety of styles, the right way.”

The plan to get the best musicians and target the high end of the market has paid off handsomely. “We’ve done all sorts of celebrities, parties for Prince Andrew, President Clinton,” says Jerry.

“I love Bill Clinton. We played for him here while he was president, and he just hung with the band for about half an hour, talking music, about his saxophone, the mouthpiece, about how he loves Ray Charles, and so on. He was nice.” Of course, there are other reasons to love Bill Clinton too, besides his affability. Being able to drop his name is good for business, as Jerry admits. “I’m good enough for the president. That’s a rep I can market, and that opportunity could only have happened here, at that time. And I could not have made my business without Martha’s Vineyard. I became known because of destination weddings. The people that were hiring me here then hired me in New York, then hired me in Palm Beach, then hired me in Aspen, then hired me in Paris, and so on.”

No doubt about it: Jerry Bennett has come a long way since the dark days of the Pampers spots. Now people are ringing up, offering money to secure a booking a year or more in advance.

“I feel blessed these days,” he says. “I struggled a lot. There were a lot of times when I had a calendar with nothing on it but white.”