Jerry Bennett is rapping Dr. Dre’s verse of Blackstreet’s “No Diggity” and the crowd is loving it. He grooves his head to the beat and beads of sweat drip from his hair onto his damp blue shirt and white pants. It’s the first time he’s left his drum kit since the party started an hour ago. He had to for this song. Hip-hop is his favorite genre of music, and he knows every word of “No Diggity” by heart. He takes off his tan suit jacket and tosses it to the side as he croons out the chorus, “I like the way you work it.” The twinkle in his eye is almost visible through his Blues Brothers sunglasses. He’s in his element and loving every second.

Once the song ends, a sparkling black vest–clad bandleader takes the microphone and introduces Bennett as the real leader of the event’s five-piece band, The Sultans. He’s also the man whose playlist has kept a party-tent full of people shuffling across a dance floor during the drizzly July evening outside the Captain Flanders House in Chilmark.

“Everybody knows Jerry Bennett,” declares the bandleader.

The next song is something completely different, “My Girl” by The Temptations. Bennett slides back to his drum machine, lightly pumping his fist to the rhythm.

After another hour of jams ranging from Motown to today’s Top 40, the band takes an intermission and Bennett walks over, glass of white wine in his hand. “I need to take a leak,” he says, “and then we can talk.” I follow him to the front door of the Captain Flanders House, up a narrow staircase, and into a dark bedroom. He uses the bathroom and then slumps into a chair in the corner of the room, showing his first signs of exhaustion of the night. He’s well tanned and clean-shaven with short, dark brown hair that he slicks back behind his ears. Slap on a fresh suit and he could be mistaken for a member of the Rat Pack. He lets out a sigh and gazes out the window.

The past twelve months have seen performances in Los Angeles, Dallas, Houston, San Antonio, Chicago, New York City, and more, he says. “The Sultans do 200 parties a year. I play twenty to twenty-five of them. Our shtick is entertainment. Great singing, a great groove, mix of songs....we love what we’re doing. People get a guaranteed party they know is going to be killer.”

When Bennett formed The Sultans (formerly known as The Sultans of Swing) with some of his buddies on the Vineyard in 1993, the band’s tour lineup was primarily local bars like The Ritz Café and one wedding a month, with Susan Tedeschi of the Tedeschi Trucks Band as their lead vocalist. He called them The Sultans of Swing because of their distinctive big band sound that could oscillate between Frank Sinatra and James Brown covers. With the Island being a hotspot for political titans to hold events, it didn’t take long for one of them to give Bennett a call with a gig that would become the band’s breakout.

“Someone told President Bill Clinton that we were the only non-roots band on the Island and that we played soul and black music,” Bennett recalls. “The Clintons danced the whole night. They’re pretty good dancers. That’s when shit started falling into place in the Northeast.”

Word spread quickly. The Sultans were the band to book for a guaranteed rave, no matter the generation of guests or event type. A Woodstock-themed acoustic pool party in Sonoma? Check. A Labor Day Island wedding where Taylor Swift was the maid of honor? Yep. Their status as presidential favorites also grew with a tour lineup that included playing parties for the Bushes, Clintons, Obamas, and even the Trumps at Mar-a-Lago.

Fast forward two decades to Jerry Bennett Entertainment, a band-for-hire empire with eight bands, nearly 100 employees, and a 600-song deep list of covers. Bennett is the owner, creative director, and DJ, and the hits just keep on coming.

Over the course of one summer weekend, Bennett says The Sultans could be bringing down the house up and down the eastern seaboard from backyard pool parties in Florida to Island fundraisers such as A Taste of the Vineyard. You won’t find pricing on The Sultans website. Bennett isn’t into that. He says he prefers the personal touch of working with each client to nail down the size of the band and overall tone of the party they want, then figuring out what price works best for them. Depending on the details, he says parties can be as “cheap” as $3,200 or go up to $35,000 for the whole shebang if the band needs to be flown out and put up in a hotel for the weekend. He says he doesn’t advertise. He lets his clients do it for him.

“Every year it gets better. We’ve never had a down year,” he says. “I think we’ve carved out a niche. Few bands can compete on this level. The volume has been incredible. I won’t say our gross earnings from August....everyone would freak out.”

The everyone he’s talking about is Bennett’s competition, which he says is practically nonexistent. Besides, he’s not a competitive guy. Sure, there are other big bands for hire that can belt out pop music covers and keep people on their feet. But Bennett says they’re focused on the flash while he’s mixing and matching the ingredients to his “secret sauce.”

“They fill one niche and I fill another,” he explains. “My business plan is to kill it at hip-hop. I’m taking old songs and putting a new hip-hop twist on them. They just have lyrics and vibe that have something magic about them. They encapsulate timeless emotions.”

Bennett knows that on your big day you can’t have your Phish-head cousin’s iPod as the evening’s entertainment. He knows what your guests really want to hear. He’s studied the airwaves from the most recent Billboard chart to summer hits going back to the 1950s. He’s watched crowds react, from indifference to full-on losing their inhibitions, and honed his craft.

“Some people want Dave Matthews. I have to protect them from themselves,” he jokes. “I look for songs with, like, a billion hits on YouTube. Five to six months later, if they are still on rotation, I know they won’t go away. I get everybody to learn it. We all FaceTime and rehearse. It’s like moving a battleship.”

It hasn’t been all calm waters and smooth sailing, however. Several members of his crew abandoned ship when he went through a divorce five years ago and he started neglecting his business relationships as he dealt with the aftermath. All of his contracts were handshake agreements, so it was easy for band members to make a clean break and convince others to join them. “It was a crisis,” he recounts. “The wheels started to come off. I didn’t do personnel stuff. A couple of key people quit. When leaders quit, the followers follow.”

The camaraderie of other band members kept the battleship afloat and Bennett quickly found a wealth of fresh new talent eager to apply for a job where they got to travel and have a guaranteed crowd at every performance. Every year he hired more and watched them go from nervous karaoke night regulars and fifth-chair orchestra musicians to a super group that could make Elvis gyrate in his grave.

“I think of it like, if we walk out on stage and it’s a nine, if we can’t make it an eleven, what’s wrong with us,” Bennett explains about The Sultans mindset. He prides himself on never missing a show, recalling a time he came close when The Sultans tour van got stuck in traffic outside a, not kidding, Dave Matthews Band concert in Connecticut on the same night as a Sultans gig.

“We ditched the van and carried our shit a mile down to the show,” he says with a chuckle.

Then there are the hurricanes. It’s his biggest fear, though not because of their capacity for destruction. He made a schedule, damn it, and now he’s stuck in a bar on Nantucket buying rounds of drinks for his band until 5 a.m. because there’s no beds to crash on. But hey, the show still goes on, no matter the elements.

“Everyone wants to get married during hurricane season. If your guests can make it, we can make it,” he promises.

Before recently moving to Palm Beach, Florida, full-time, Bennett worked out of a wood cottage he called The Outhouse next to the pool behind his Edgartown summer home. On another rainy day a few weeks after the event at the Captain Flanders House, he’s sitting at his desk surrounded by two large computer screens and watching CNBC’s Mad Money out of the corner of his eye. His German shepherd Mia is curled up nearby. He just read some tweet from Tesla CEO Elon Musk and is shaking his head.

“I had Twitter for a while. I could see its dangers,” he says. He’s wearing his typical work-from-home style: jeans and a gray T-shirt along with his father’s Freemason ring on his right hand. He’s working on matching his musicians with gigs and gigs with playlists. “It’s Jenga, it’s a puzzle,” he explains. He logs out and takes me to the main house, into a large room with furniture and instruments strewn about from moving preparations. He sits at a Steinway piano in the corner, his mother’s, and plays a few notes.

“I want to get better at the piano and play again,” he says. “Growing up, my mom was a musician and a dancer. [The Count Basie Orchestra] would come to the house to jam.”

He smiles and looks off, recalling mornings waking up in his home in Scranton, Pennsylvania, to an alarm of jazz and swing music. His father Richard, a businessman and jazz lover, would invite the Count Basie crew over for after parties in the Bennett basement that would often go on until the wee small hours of the morning. His mother, Helen, would dance along. Instead of being sent back to bed, Bennett was allowed to join in on drums, which he quickly took a shine to. By the time the family moved to New Jersey in 1965, Bennett could play piano and saxophone, but drumsticks still felt best in his hands. He studied jazz percussion at the New England Conservatory of Music in Boston for five years and then moved to New York City, determined to become “the world’s greatest drummer.”

He landed a few studio gigs, playing sessions with the likes of Duran Duran and Grace Jones, but most days the phone never rang and rent payments were always on the mind.

“I was just stressed, man,” he recalls. “You do a six-week record and go home again with no job. I didn’t like having no say in my future.”

To make ends meet, he would play drums at weddings during the day and write jingles for commercials at night. Turns out he had a knack for songwriting and landed work with Coke (and Pepsi), Jeep (and Ford), and Red Stripe beer, for which his jingle got airplay for six years. He also contributed music to horror movies A Nightmare on Elm Street and Children of the Corn.

It got him a paycheck, but the problem was someone else was writing them. “I was putting my fate in others’ hands,” he remembers. “I just wanted to have a life, and I could see that wasn’t going to happen. Now I control my destiny.”

Controlling his destiny starts at 6 a.m. sharp and goes until 2 p.m. before he takes a nap, works out, then goes back to work for another hour, seven days a week. On the weekends he sets up shop on a wide, white couch in the main room of his house so he can watch football games while he checks his emails. He gets a lot of those. He says reading them is the “highlight of his week.” We sit down on the couch and he opens his laptop back up to show me what he means.

“These are emails of some band members congratulating each other for a gig,” he says, pointing at a chain of messages. Others are from clients with rave reviews and promises to recommend Bennett to their friends. He pulls up Google to show me the company’s 4.8 WeddingWire (basically Yelp for weddings) score, another one of his points of pride, though with one exception.

“It’s not five because of one lonely one star rating,” he remarks nonchalantly, though it clearly irks him.

He sets the laptop aside and starts giving me a tour of the house, leading me up a staircase lined with family photos. Bennett is in most of them, flashing a contented soft smile, the look of someone who’s figured it out and can relax. He’s often standing next to his two kids, Caley and Cooper. They’re both in college now. Upstairs, their wing of the house is sparse and quiet. Really, the whole house is. Bennett has a girlfriend in Florida who occasionally visits, but most days he’s alone. He doesn’t mind. He’d rather be home than always on the road partying, missing the things that really matter. It took the loss of his father three years ago to force him to realize what those things were.

“At my father’s funeral, I was more worried about my career than the funeral,” he recounts. “I had also missed a thousand Little League games, recitals.…” He looks down and shakes his head. There’s a pause and then he looks me right in the eyes.
“I don’t regret it,” he says with conviction, adding that he speaks with his kids every day on the phone now.

We head back to the couch and sink into it, listening to rain pattering gently against the window. Mia walks over and gives Bennett a nudge. He gives her a pat and rests his eyes.

“Life will define you,” he murmurs to no one in particular.

Back at the fundraiser, Bennett leaves the stage after four hours of jamming, drumsticks in his back pocket, looking like he just finished running a marathon. People begin shuffling out of the tent into the night, poking fun at each other’s awkward dance moves. Bennett lingers, looking over at his crew breaking down the stage. Somewhere along the East Coast, it will soon be set up again with a whole other band. Bennett may not be there, but he’ll read the emails. The show will go on.

He smiles and leans in with one more piece of wisdom to share.

“I believe there’s two kinds of music: good and bad,” he concludes. “I don’t need a board, I have the crowd. It’s direct, not digital. I enjoy this so much more.”