Should you find yourself at a local bar, a well-made rye Manhattan in your hand, whisper a “thank you” to Brother Cleve before you take that first sip. Often called the godfather of Boston’s cocktail scene, the musician, DJ, bartender, mentor, pursuer of singular passions, and raconteur extraordinaire died suddenly last week. He was 67.
“It is not overstating it. Godfather was a term of respect,” says Jackson Cannon, a bartender who has helmed cocktail destinations such as Eastern Standard and The Hawthorne. “It doesn’t even get to how much all of what we did came out of his enthusiasm. When people look at the foundation of what we have, it all comes from Cleve. It really does.”
Brother Cleve grew up in Medford as Robert Toomey — the nickname came later, a souvenir of his involvement with the parodic Church of the SubGenius. He came of age in the Boston music scene, frequenting legendary Kenmore Square rock club The Rathskeller: “I always drank Manhattans, even as a punk rocker at The Rat in the ‘70s,” he told me once in an interview. And music was where he first made his mark, playing keyboards with bands such as Combustible Edison and the Del Fuegos.
It was while on tour with the latter, one fateful day in 1985, that he had an epiphany. The band was having lunch at an old-school diner in Cleveland. “The back page of the menu said, ‘Try a refreshing cocktail!’ There were probably 75 or 80 drinks on it. I never knew there were that many cocktails,” he said. “I remember looking at the other guys and saying, ‘What the hell is a Sidecar?’ I went out and bought a bartending book right after.”
It would turn out to be a seminal moment for Boston’s cocktail culture. Cleve went on to bartend at Hoodoo Barbecue, introducing old-school cocktails to a Bud Light crowd in the shadow of Fenway Park. And he made connections between the worlds of music and drink, twin passions with a natural affinity. Combustible Edison, for instance, was a pioneer of the groovy lounge-music revival movement Cocktail Nation. “It was the height of grunge, and here they are making music and mixing proper martinis on the stage across the country an entire decade ahead of the craft cocktail revival,” Cannon says. Wherever Combustible Edison traveled, they would teach bartenders how to make the drinks they loved.
Brother Cleve also presided over Saturnalia, a weekly lounge night at the Lizard Lounge in Cambridge. Cannon was the booking agent there. Misty Kalkofen (Drink, Brick & Mortar) was slinging drinks, her first bartending gig. Brother Cleve began teaching her to make Manhattans, martinis, Sidecars. “I owe so much to him,” says Kalkofen, now director of education at hospitality-focused nonprofit Another Round Another Rally. “He was such a mentor for me. He bought me my first bottle of rye whiskey back in the day when you couldn’t go into any liquor store and get it.” They would close down the bar, then go back to someone’s house and dig through old cocktail manuals in search of gems to try. At some point, Cannon, Kalkofen, Brother Cleve, and his wife, Diane, shared a house in Somerville. Their friend John Gertsen (No. 9 Park, Drink) would come by, and the bartenders would mix up variation after variation of drinks to figure out what they liked best. They called themselves the Jack Rose Society, after the first cocktail they experimented with.
Meanwhile, a bartender named Patrick Sullivan was opening his own cocktail spot in Cambridge, and Brother Cleve’s name kept coming up. So Sullivan tracked him down and brought him in. Cleve was on the bar the night the B-Side Lounge opened. Kalkofen soon joined the crew. “That was a bar that changed the drinking landscape of Boston,” she says. “Cleve had a huge, huge part in that, working with Patrick and guiding him on recipes and menu development.” He was a great bartender, if not a particularly efficient one: “He had such a following. He loved to tell a good story; he’d get so engaged telling it. We used to joke that he was really good with the five guests he was serving.” (In turn, everyone who met him has a great Brother Cleve story: the time the bar at Cafe Montmartre in Madison, Wis., got set on fire at a Combustible Edison gig because staffers were making the band’s namesake flaming cocktail; the time Cleve and a bunch of other bartenders played an impromptu musical session at The Hawthorne; the time he showed someone around his favorite spots in New Orleans; or took someone else to his favorite Chinese restaurant, or … well, I promised I wouldn’t tell that one.)
The B-Side became one of the torchbearers for classic cocktails, and the bartenders Brother Cleve befriended, mentored, and worked alongside grew into the next generation of top talent in the area’s best bars. “If there’s a cocktail family tree, Cleve is at the very, very, very top of it. In terms of making an impact, his place is undeniable,” says Sullivan, now co-owner of the Bluebird Bar in Newton. “All the young kids today, they all really looked up to Cleve. More than anything, Cleve loved to have a nice cocktail. He loved it, like in a romantic, beautiful sort of way. And he would go into their bars. He liked sharing his knowledge. He was just brilliant. He knew everything. Like the dining-car diners of New Jersey: He could tell you 50 current ones and the top 25 ones he misses that are no longer there. He was the doctor of kitsch and sentiment. He loved things that were going away.”
When Gabriel Bascom and Wusong Road chef-owner Jason Doo launched the New England Tiki Society at the end of 2021, one person’s name kept coming up, again. Brother Cleve provided the music at their second meetup in July, helping the founders navigate things like sponsorship and turnout. The event sold out. “It would not have happened without his experience,” says Bascom. “I would not have realized there were as many tiki people in the area if Brother Cleve hadn’t been there to connect everyone.” Cleve never stopped teaching and sharing; when he died, he had just appeared at Tiki by the Sea, a three-day educational event in Los Angeles. He was also a partner in New York cocktail bar Lullaby, which opened earlier this year. (He met one of his 20-something partners, Harrison Snow, when Snow was bartending at Paris Creperie in the Seaport, for which Cleve designed the cocktail program.)
Force of coolness, bridge between generations, keeper of cocktail lore, OG influencer, and generous mentor, Brother Cleve helped shape Boston’s hospitality scene. “His enthusiasm for everything was the real hallmark. It always came through,” Cannon says. “He knew about so many different things like an expert: music, or drinks, or he was just dedicated to the dying cool, casual food of the country. He attacked subjects as if to preserve them. He was so ready to share that information. I just wish he was still doing it.”