Brother Cleve Is a Difficult Man to Define

Editor’s Note: On September 10, 2022, Brother Cleve died while traveling in Los Angeles. He had recently opened a bar, Lullaby, in New York City.

The cocktail renaissance has had its share of godfathers. Dale DeGroff got the ball rolling in New York when he unfurled a menu of nearly forgotten classic cocktails at the Rainbow Room in the late 1980s. Dick Bradsell mentored hundreds of young London bartenders through his work at Fred’s Club, Atlantic Bar & Grill, and a dozen other bars. Paul Harrington brought his research into cocktail history to bear during his short stints during the early ’90s at Enrico’s and townhouse Bar and Grill in the San Francisco Bay area. These were distinct men with very different histories, but they all had one thing in common: They were bartenders.

Brother Cleve, the unquestioned founder of Boston’s modern cocktail revival … isn’t a bartender. He is … well, it depends on who you’re talking to.

Brother Cleve, the unquestioned founder of Boston’s modern cocktail revival, on the other hand, isn’t a bartender. He is … well, it depends on who you’re talking to. Ask music people, and they’ll remember him as the keyboardist for the Del Fuegos, the 1980s garage band, or as a member of Combustible Edison, the ’90s retro lounge act out of Providence, Rhode Island. They may also know that he plays a decent accordion, an instrument he picked up after hearing a Clifton Chenier record. 

Ask Boston’s 24-hour-party people, and they’ll recognize Cleve as one of the city’s leading DJs, a man who owned 20,000 records until he recently decided to pare down his collection. Now, he only has 10,000. But ask any Boston bartender under the age of 50, and you’ll get a different story. They’ll tell you of a Cleve that attracted curious attention by persistently drinking Manhattans in the ’80s; a Cleve that special-ordered them their first bottle of rye whiskey; a Cleve that sat them down for a serious, considered tasting of quality tequila brought back from Mexico; or a Cleve that taught them everything they know about cocktails. “He’s such a distinct personality,” says Jackson Cannon, bar director of Boston’s Eastern Standard, among other spots, and one of the first bartenders to learn about cocktails at the elbow of Cleve. “He can go very deep into a sub-genre of music and connect it to bar culture in a way very few people can. He brought a maturity to all this. His artistic sensibility and his libertarian streak all come together in a very unique way of relating everything.”

Boston bar luminaries like Cannon, Kalkofen, and John Gertsen (formerly bar director of the noted cocktail den Drink) kept the legend of Brother Cleve alive during the late 2000s, when the man himself was not much in evidence in bar circles.

“That’s one of the best things about Cleve,” echoes bartender Misty Kalkofen, another protégé. “He’s definitely not one professional in any kind of way.” Boston bar luminaries like Cannon, Kalkofen, and John Gertsen (formerly bar director of the noted cocktail den Drink) kept the legend of Brother Cleve alive during the late 2000s, when the man himself was not much in evidence in bar circles. In 2007, just when the cocktail revival was shifting into high gear, Cleve was diagnosed with tuberculosis and gave up drinking. During the subsequent period of recovery, he focused on his DJ work and receded into the back eddies of the cocktail current.

Recently, however, he’s made a comeback. He took a few guest bartending shifts for Big Night Entertainment Group, which owns several restaurant and bar properties throughout Boston and Connecticut. That turned into a full-time gig as the outfit’s cocktail ambassador. as a result, a whole new generation of Boston bartenders are being exposed to Cleve’s sui generis mix of skill, knowledge, and perspective. “Instead of retiring, I’m starting a whole new aspect of my career,” marvels Cleve.

Brother Cleve learned about cocktail culture on the road, while touring with bands. He knew about Rob Roys and Daiquiris; his parents drank them during his childhood in Medford, Massachusetts. But it wasn’t until he was confronted with a cocktail list at Shorty’s Diner in Cleveland in the mid-’80s that he realized how much he didn’t know. There were 100 drinks on the menu. He turned to the bass player of the Del Fuegos and asked, “What the fuck is a Sidecar?”

Then the quest began. At each tour stop, when his bandmates went back to the hotel, he would head out in search of bitters or comb local bookstores for out-of-print cocktail manuals.

Cocktail culture fit in seamlessly with his tenure in Combustible Edison, a group led by characters as quirky as he, including a guitarist self-dubbed The Millionaire and singer Miss Lily Banquette. The combo was so tuned into the suave ’50s aesthetic that it had a namesake cocktail (brandy, Campari, lemon juice), which was mixed up on stage during sets. “As The Millionaire said, drinking cocktails was the most punk-rock thing you could do in the ’80s, because nobody did it,” Cleve says. “Doing all these old-school cocktails was an act of defiance against society.”

By the time bartender Patrick Sullivan bought a notorious old Somerville dive called the Windsor Tap, with the aim of converting it into a cocktail bar, Cleve had forged a local reputation. An article in the Boston Globe called him “The Lounge King of Boston.”

The B-Side, as the Windsor was rechristened, opened in 1998 with Cleve slinging classic cocktails to a crowd heavily drawn from the music world. The Windsor Hi-Lo was a can of Schlitz and shot of Chartreuse—years before such unorthodox boilermakers became commonplace. Soon, Kalkofen, whom Cleve had tutored at the Lizard Lounge, joined him behind the bar. What few budding mixologists there were in Boston made the pilgrimage to the spot. 

Soon after, Cleve and a few of his apostles founded the Jack Rose Society. The group would get together to workshop an old cocktail, making a couple dozen versions of, say, a Ward Eight, until they found the best recipe. It was a febrile time for Boston bartending.

Given his mythical status and colorful history, one might expect Brother Cleve to be an imposing eccentric. Instead, he’s no more intimidating than, say, a slightly hipster-ish substitute teacher. 

Given his mythical status and colorful history, one might expect Brother Cleve to be an imposing eccentric. Instead, he’s no more intimidating than, say, a slightly hipster-ish substitute teacher. A man of medium build and gently garrulous demeanor, he is typically dressed in retro clothes and a porkpie hat, and he looks like the sort of guy you might run into at a home tiki party. “Cleve has always been the same cool, down-to-earth person, no matter who he’s talking to,” says Kalkofen. 

And the man does like to talk. Give him an hour or two (which he can ably fill) and his many layers begin to peel back. You might learn how he met Juan García Esquivel, the lounge-music master, in Mexico; how he befriended the members of Devo; how he became obsessed with Bollywood music, traveled numerous times to India and put out two compilations of Bombay disco music; how he was such a regular at New Orleans’ storied dive, Saturn Bar, that the owner took phone messages for him; or how he performed on a punk sports talk show in Boston as a character that mixed parts of wrestling manager Captain Lou Albano, comedian Rudy Ray Moore, and evangelist Jimmy Swaggart.

That character, by the way, was named Brother Cleve. The radio stint is only half the story behind the adopted handle of the former Robert Toomey. The quasi-religious moniker also harkens back to his membership in Church of the SubGenius, a fake religion founded in the ’70s that worshiped J.R. Bob Dobbs, “the world’s greatest salesman.” 

These days, Big Night Entertainment is keeping Cleve busy. The group plans to open several new places in 2017, and Cleve will be handling the cocktail lists from the ground up. He no longer needs protégés like Cannon and Kalkofen to remind bartending newcomers who he is, as he discovered at a recent party. “Every kid in town was there,” he recalls, and all of the new bartenders wanted to buy Boston’s bar mentor a drink. “I’m working in the industry now. I wasn’t for years. I was …”—he struggles for the right word—”a personality, I guess you would say.” Yeah. You could say that.