Brother Cleve Shares What Bartenders Can Learn From Musicians

Headshot of Brother Cleve
Brother Cleve has had a foot in both the music and the cocktail worlds for decades.

It seems Boston booze legend Brother Cleve was always destined for cocktail greatness. You can thank his grandmother for that. Her love of whiskey and Manhattans made with Canadian Club were his first cocktail memories. The young teen would sneak sips when his parents were away or when his grandfather, a recovering alcoholic, wasn’t at home. His grandmother would hide whiskey around the house, as Cleve discovered one afternoon while seeking a place to stash his own contraband, cigarettes. The two made a pact that neither would tell the other’s secret as long as he still got a few sips and she a few drags.

Cleve’s love affair with cocktails continued throughout the seventies, eighties and nineties playing keyboard in bands like the Del Fuegos and the cocktail-evangelizing loungecore act Combustible Edison. While his punk rock idols and musical comrades were chugging a few beers before, during and after shows, he preferred sipping on Old Fashioneds and Manhattans. Back home in Boston, between gigs and bands, he would bartend to make ends meet.

“I just wanted to play music and bring classic cocktails to an uncaring world. I was on some weird mission. But, it was cool to go on tour and come back to the bar and be like, yeah, I’m in this band that opened for INXS and Tom Petty, and I’m sipping on these obscure cocktails like it’s my job. It’s hard not to let that go to your head,” he says.

“My music and bar careers in those days were full of fits and starts. For a young guy, your ego bruises easily. You don’t have a lot of patience. I kept pushing the limits behind the bar, hoping someone would notice me or care about what I was doing with cocktails.”

As his love for and knowledge of cocktails grew, so too did his reputation around Boston for being the go-to drinks guy. In 1998, ten years after he first stepped foot behind the bar, Cleve was tapped to develop the menu for Boston’s premier craft cocktail bar, B-Side Lounge. It was here he would finally launch the city’s drinks revival.

Fast-forward thirty years through numerous bar jobs, brand ambassadorships, and musical projects, and a much-wiser Cleve is skillfully straddling the line between cocktails and music — only now as its elder-statesmen and godfather of a fully-evolved Boston cocktail scene, which includes his protege Misty Kalkofen and a bass player he met twenty years ago named Jackson Cannon.

He talked about the parallels between music and bartending at Tales this summer in “Letters to a Young Bartender,” and what he believes are the keys to longevity in the bar industry.

The Startender

“One of my biggest issues as a young bartender was ego and forgetting that, like a band, a bar is one big team no matter who’s out in front,” Cleve tells us.

Cleve recalls coming off tours and waltzing into the B-Side Lounge where he was only working a couple of shifts a week due to his travel and rehearsal schedules. Regulars, fans and even the press would gather at the bar to talk with him, helping to fan the flames of a growing ego.

He remembers two regulars in particular who would come in with index cards full of cocktail recipes they wanted him to create while they picked his brain and he pontificated on the finer points of the classics. One afternoon while “holding court,” he caught his young mentee Misty Kalkofen out of the corner of his eye frantically working service.

“I could feel the daggers. She didn’t have to speak. I knew I’d messed up. I was letting my ego drive my bartending. I wasn’t pulling my weight. That’s the day I learned to say 'excuse me' to guests.”

While Cleve admits a little bit of ego is necessary in bartending, you have to learn to manage it. The key to a successful bar program rests not with one bartender but with everyone working together behind the bar.

“It’s like someone has a guitar solo in the middle of a song, but that musician is still being backed up by the bassist and the drummer. Without all the players in sync, the solo sounds disjointed and hollow and the song falls flat.”


Being a bartender with a reputation for making creative cocktails brings in more than just press and regulars, it also brings in groupies. Recognizing the line between regular and groupie, friend and hanger-on can be difficult and is blurred further by a flattered ego and alcohol. It’s a skill Cleve believes is only mastered with time, experience and unfortunately, a few missteps.

“Bartenders in many ways are the rockstars of today, especially if you’re really good. You have local or national followings — groupies and fans. People come to see you put on a show and drink your drinks. Everyone wants to talk to you and be your friend. Knowing the difference between the star-chasers and those who genuinely admire your work can be difficult.”

Cleve advises keeping the bar between you and your guests until their intentions are clear: politely declining after-work drinks, buying you shots or even slipping you their phone number.

Original compositions vs. arrangements

Cocktails are all adaptations of some form of classic or basic formula, and Cleve says coming up with your own creations isn’t necessarily the true mark of a masterful bartender.

“It’s like saying, if David Bowie covers Pink Floyd, he can’t be a great musician. The Beatles covered Chuck Berry, does that make them bad musicians? No. To me, arranging music is just as much of an art form as creating original compositions. It’s the same with cocktails.”

Cleve calls his arrangements remixes, and proudly lists them as such on his menus.

“You can give ten bartenders the exact same recipe and it will come out ten different ways. The arrangement is yours. Don’t poo-poo making a Manhattan because you didn’t actually create the recipe. You’re paying homage with your own arrangement — even choosing the base spirit is your unique interpretation.”

Everyone plays a part

In researching a story recently for Eater Boston, Cleve visited one of the last true dive bars in the city. He says it and the people who work behind the bar there are a dying breed: the old-school, shot-and-a-beer, no frills kind of joint where hospitality, rather than mixology, rules the day.

After 30 years in the business and reviving cocktails in Boston, Cleves says he has learned one important lesson...we don’t need mixology at every single bar. Just like musicians aren’t expected to know how to play every instrument, not every bartender or bar has to make martinis and Old Fashioneds.

“Bars are about camaraderie and fellowship, and bartenders are the hosts, whether they’re serving complex cocktails or classics in a beautifully designed bar or Bud Lite in a beach shack. The beauty of this industry is there’s room for all types of bars and bartenders, and they don’t all have to be under one roof.”

Cleve’s godfatherly advice

“Bartending is hard work. It’s physically and mentally demanding. Work your way up the ladder and really learn and appreciate the business. Barback, work crappy shifts, do prep, wash dishes, read every book you can get your hands on, ask questions and really practice your craft.”

“Remember, whether you’re the star or in the supporting cast, it’s not a movie, a band or a bar without you.”

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