Jerry Bennett lives on Martha’s Vineyard, but his band — The Sultans of Swing — plays all over the country, from California to Florida, Texas to Boston, and just about everywhere in between. As a matter of fact, on any given day, the band may be found playing in as many as five different locations. That’s because The Sultans are not just a single musical unit. They are more of a conglomeration — a brand that encompasses upwards of 100 musicians, including 15 different singers, performing under the same name, with Mr. Bennett as the maestro behind the large and growing group of musicians.
In 1995, Mr. Bennett moved to the Vineyard from New York, where he was a successful studio musician and songwriter. He played the drums on gold records for Duran Duran, Yes, Grace Jones, “And other 80s dinosaurs,” as he puts it. He also wrote music for national ads for Coke, Pepsi, Jeep, and Ford Motors, among others. Like so many others who have settled here, a weekend visit inspired a permanent relocation. “I noticed that there were a lot of rich people here who needed music for their events,” he says.
Mr. Bennett paired up with future Grammy nominee Susan Tedeschi and played regularly at The Ritz in Oak Bluffs. Eventually he formed the original Sultans of Swing, so named because the band specialized in big band swing music, which was enjoying a revival at the time. The Sultans quickly became a favorite for weddings and other gatherings and during the short Vineyard event season they couldn’t keep up with demand. Says Mr. Bennett, “We started duplicating ourselves because of the seasonality of the Vineyard.”
Today, thanks to word of mouth, The Sultans enjoy nationwide popularity, especially in upscale resort areas. Says Mr. Bennett, reciting his upcoming itinerary, “On any given weekend I could have a party at the [Florida] Keys, Martha’s Vineyard, New York City, Dallas, and Boston.” He flies to gigs every weekend and spends weekdays with his wife Elliott, who is the head of the high school’s science department and two kids Caley, 14, and Cooper, 10, who both play music, at their Edgartown home.
The Sultans of Swing musicians are primarily based in Boston and New York. Mr. Bennett has managed to recruit an impressive lineup of talent through connections fostered during his former career and his time studying at the New England Conservatory of Music. “Once you get into the loop of the best guys, you’re in the loop,” he says, noting that he gets referrals from the members of his current lineup. Vineyarders include bassist Hugh Burrows and singer Joanne Cassidy, who he refers to as “the Island’s darling.”
Not only does the outfit encompass a multitude of talent, they also represent a number of different musical genres. Their range covers big band swing, top 40, classic rock, Motown, and just about every other style imaginable. Mr. Bennett matches his musicians with the requested genre and play list. The multi-faceted band is able to accommodate requests.
Mr. Bennett gives two examples of unique gigs. For one wedding, the band played nothing but music from a single Miles Davis record, “Kind of Blue.” For another he provided musicians who played only Brazilian bossa nova. Some clients want it all, and The Sultans can meet that request as well. Says Mr. Bennett, “In one set they could hear Jay-Z, Louis Armstrong, and Tom Petty.”
The Sultans, as Mr. Bennett now prefers to refer to the band, have played for four American presidents — both Bushes, Clinton and Obama — numerous celebrities and, according to Mr. Bennett, they are Donald Trump’s favorite band. After hearing them play at a fundraiser at Mar-A-Lago, The Donald raved about the performance and, during his brief Presidential bid, planned on hiring them as his campaign band. The Sultans have performed with some big names in the music world, including the Blues Brothers. “Jeffrey Osborne joined us in Lambert’s Cove for a soul wedding,” he says. In September, the band will back up Diana Ross for a show in Dallas.
For the past seven years The Sultans have entertained the crowd at the popular Taste of the Vineyard Gourmet Stroll in June. Mr. Bennett stresses that they always play for cost, as the event benefits the Martha’s Vineyard Preservation Trust. “We do it for the love of our community,” he says. He tries to add a new dimension to the show each year. For the upcoming Taste, he will be including some of his newest recruits — hip hop musicians from New York.
Ever-evolving, “The band that Jerry built” will no doubt continue adding new members and new sounds and generating new fans in new locations. And Mr. Bennett sees the tradition continuing into the next generation. “My hope is that my kids will carry on The Sultans.”
Gwyn McAllister of Oak Bluffs is a frequent contributor to The Times.