Meet Dan Blakeslee, the Toothless Troubadour of a Gentrifying Somerville

Photo by Kyle Clauss

They put Dan Blakeslee in a parking lot festooned with weeds, in front of a bus bearing the giant likeness of a sneering muskrat. Its carotene teeth are the same color as Blakeslee’s shirt, which clings to his wiry frame in the humidity. It could rain on the Ignite! Festival in Union Square any second, so Blakeslee tunes his guitar with some uncharacteristic urgency.

Stage-right from Blakeslee—and “stage” is an awfully generous word for his patch of asphalt, folding chair, and chain-link fence—20-somethings are shredding cabbage and carrots in a canning seminar. He introduces himself and launches into “Lazy-Eyed Girl.” A man approaches him and hoists his infant inches from Blakeslee’s face while his wife snaps a picture. Blakeslee stops mid-line and smiles politely. A middle-aged mom at her wit’s end flushes her gaggle of three squealing kids out from behind the muskrat bus, and they run through the folk musician’s performance, back to the plastic-lined picnic table, to their untouched curry dinners.

To say Blakeslee belongs here is not to say he deserves all this disrespect. He belongs in Somerville, amidst all its inexplicable quirks, strumming his guitar—its pick guard, the silhouette of an octopus he carved with an X-Acto blade—along to the Brubeckian beat of New England’s most densely populated municipality.

Not far from the muskrat, 197 Union Square has reached its tipping point, with more than half of its 30 luxury units leased. The asking price for one of its 1,061-square-foot, two-bedroom, two-bathroom apartments starts at $695,000—nearly $200,000 more than the city’s median home value.

“Somerville itself is rapidly becoming a vibrant epicenter of arts, music, and culinary excellence,” the complex boasts on its website. “Come live it!”

Blakeslee and scores of other artists who call Somerville home already do live it, and have done so for decades. If the proliferation of luxury condominiums continues at this breakneck pace, the creative class used to lure well-heeled homebuyers to the banks of the Mystic River could soon find themselves shut out of the city they call home.

• • •

I walk along the Mystic as the river it curls,
Under ice and the snow, it’s shinin’ like pearls.
The stars came with me, and a horseshoe did too.
Maybe luck will be there waitin’, in the year of the new.

• • •

I find Blakeslee in a booth in the back of Diesel Cafe in Davis Square. An Italian restaurant in Salem commissioned Blakeslee to make their placemats, so he dips his nib into a bottle of black ink and crosshatches a comic strip about a Boston terrier chasing a pizza through the cosmos.

In between shows, he sustains himself on gigs like these. A graduate of the Maryland Institute College of Art in Baltimore, his best-known work is the label for the Alchemist’s Heady Topper, an unfiltered, unpasteurized double IPA widely regarded to be the greatest beer in the world, inspiring ad fontes pilgrimages to Waterbury, Vermont, where it sells out within seconds.

“I was sitting, doing one of my show posters for a music event at a cafe up in Burlington, Vermont, and this guy kept peeking over my shoulder, and eventually said, ‘Hey would you ever want to do a beer label?’” Blakeslee says. “It was funny, because he said quietly to me, ‘Man, I’ve got this beer that I think is gonna knock people out. Everyone I’ve shared it with is kind of mystified.’”

The label is a self-portrait of Blakeslee with a plume of hops and steam erupting from his head as he takes a sip. But the real Blakeslee’s never had a beer before, and only tried the legendary brew by accident when he tried mimicking the label at a party with what he thought was an empty can.

“I got a big sip in my mouth, and man, that is potent. That is, in capital letters, POTENT, is the word. I’ve had seven sips of alcohol in my life, and I just never like that feeling—that tingly esophagus, I just don’t like it,” says Blakeslee. “I’ve never had anything against it. A lot of my friends drink and I sort of feel like I haven’t needed it this far. You know what I mean? It’s like my natural high.”

He leans in. “Wanna know the inner secret? Orange juice and molasses cookies. Not together. Orange juice—I feel like that makes me high.”

“What brand?” I ask.

“It can’t be just any brand. What’s that one, Simply…?”

“Simply Orange?”

“Yep. Or Tropicana.”

“Minute Maid is shit, though.”

“Yeah, Minute Maid is not good,” he says. “Not good.”

• • •

I walk along the Mystic, on this wintry morn.
On this coin I wish, to mend a heart that’s torn.
To the wind I tossed it, frozen it flew.
Now it rests on the ice, till spring takes it through.

• • •

This is Blakeslee’s 20th year as a performing musician and perhaps his most auspicious yet. After years of busking outside the entrance to the Newport Folk Festival, Blakeslee earned a spot on the lineup and performed onstage. He has a new car, a 2012 Honda Civic named Wanda, to carry him from gig to gig across the country, after his last steed, an “incredible lemon” called Numbnuts, split its frame going 8 m.p.h. over train tracks. “It’s the first time ever I’ve gotten a modern vehicle,” he says. “Every single car I’ve ever had has been 10-plus years old. One of my favorite longtime companion cars was my 1970 Chevy Impala that I had for four years, and I bought it for $50. I’m a sucker for a cheap guitar and a cheap car.”

Blakeslee finally got around to taking a guitar lesson, a birthday present from his jazz pianist father. “It was so great to actually learn what I was doing, because I never knew. I would play a chord not knowing what it was until this year,” he says. And the broken tooth that threatened to derail Blakeslee’s third studio album, Owed to the Tanglin’ Wind, is just about healed. In the meantime, his friend, a dentist to whom the album is dedicated, fashioned him a makeshift putty tooth so he could sing.

Blakeslee grew up on a farm in South Berwick, Maine, surrounded by music and art supplies. After a brief foray into breakdancing (“I was damn good!”), he discovered punk in seventh grade when he saw Five Balls of Power, Dropkick Murphys frontman Al Barr’s high school band, play in Portsmouth. He was 18 when he picked up a guitar for the first time and headed to Baltimore for art school.

“Both my parents have always nurtured my brothers and I to follow our hearts and do what fulfills us passionately. Music and art was always a gigantic part of my life, and they just urged me to jump in fully without any reservation,” says Blakeslee, his thumb still stained with ink. “So I’m definitely, hugely grateful to have a supportive family. Because when I went to art school, there were a lot of friends of mine that would say, ‘Yeah, well, my parents want me to become a lawyer or doctor.’”

He moved into a friend’s place in Davis Square in 1995, “back when it was cheap,” and busked on the MBTA to get by. He took a break from it when, after performing underground for eight hours without eating, his roommate found him at their kitchen table passed out from malnourishment.

Earlier, a woman leapt off her idling train at Copley Station and slipped something into his pocket. Delirious from exhaustion that night, Blakeslee found a $100 bill and a note requesting a copy of his recordings. He sent the woman everything he had and used the money to move back to Maine for a year, before bouncing around between Jamaica Plain, Allston, Brighton, and New Hampshire. He settled in Somerville a decade ago.

“I just feel so endlessly creative here by the people I’m surrounded by—musically, artistically, other ways,” he says before rattling off his favorite haunts: Groove Records, Bloc 11 Cafe, Petsi Pies, Forge Bakery, Izzy’s, the Neighborhood (whose citrus-tinged cream-of-wheat he has tried and failed to recreate).

“I’m forever charmed by it.”