On a rainless weekend morning above 40 F, you can usually find Roland Pearsall lugging a cart with chords and amplifiers in one hand and a guitar case in another. He’d be on his way to Harvard or Davis Square, about to sing his heart out for the next several hours with the voice of someone who had grown up singing on grassy plains.
In fact, Pearsall did grow up in a small town.
“I grew up in Connecticut … in the middle of nowhere with more dairy farms per capita than anywhere in the whole state,” Pearsall said.
His childhood was musical, with a father who constantly played classical rock on the radio and would sing with, what he called in an interview with Sound and Vision in 2019, “a voice that carries.”
In the same Sound and Vision interview, Pearsall recalled one time when his grandmother took him and his parents to see Chuck Berry, one of the pioneers of the rock genre, which he recalled being “the greatest show I’ve ever seen in my life.”
“There was something in his performance I felt like I intuitively understood,” Pearsall said. “He connected with the audience, and he just held the crowd in such a way, and … I got it.”
Inspired by these various influences, Pearsall began learning to sing and play the guitar himself, doing street performances starting in 2009.
Pearsall eventually decided not to become a full-time musician, instead moving from Connecticut to Boston in his 20s, and pursuing a graduate degree in higher education administration at Boston College.
However, his love for the art persisted and he grew as a musician, picking up harmonica, drums and several other instruments. Not long after moving to Boston, he decided to take this passion a step further.
Boston, by the late ’60s, was gaining reputation amongst the rock circles for the whirlwind speed of its musical culture’s evolution. Throughout the rest of the 20th century, it attracted people from all genres, and many artists performed in public spaces like Harvard Square. The city of Boston was, and very much still is, breathing in music.
So perhaps, there was no better place than Boston for him to launch his career as a part-time street musician, seven years ago.
Pearsall performs throughout most of the seasons, as his unconventional temperature tolerance allows him to perform as long as it’s not raining and or below 40 F.
“I'm usually the type of person in 57 degree weather walking around with no jacket, and everybody else is shivering,” he said.
Being a multi-instrumentalist with an openness to dozens of genres, Pearsall’s act evolves constantly. Each year, he learns approximately fifty or more songs, expanding his already expansive repertoire of several hundred pieces.
During weekdays, Pearsall works as the director of institutional research at a small private college in Boston.
“I guess it’d be best described as a cross between data science and business intelligence,” Pearsall said. “I do a lot of research of what is going on with our college … [And when] the higher-ups want to know what's going on, I’m one person they go to.”
Then, on Saturday, around 11 a.m., he goes to either Harvard Square, Davis Square or even the Boston Public Garden, depending on foot traffic and the number of other performers.
Upon arrival, Roland Pearsall sets up his trusty microphone and Roland amp and takes his guitar out of its case. The case serves as a small advertisement space with coasters to hold down money and battered A4 posters detailing his social media information.
“I never have a setlist,” Pearsall said. “It’s always really off the cuff and off the top of my head, whatever I feel like at that moment.”
His performances are predictable in other ways — friends from his workplace would drop by, passing musicians would join in and audience members drop items in his guitar case that are not money.
“I’ve got some of the weirdest stuff too … I’ve gotten alcohol, I’ve had cigarettes, all kinds of stuff like that. I don’t smoke,” Pearsall said. “One time somebody put what looked like some kind of pastry, and they taped a dollar bill to it and they dropped it … and it was actually touching the actual food item.”
A lot has changed in Pearsall’s life since he first began doing street performances.
After years of effort, he released his first, self-produced album in 2015 titled “Sell Your Soul,” and he is currently working on a second album. Since he started performing, he has watched the city and people change, and has been interviewed, gained fans and played at private events.
Pearsall, who is close with his family, is not thinking of becoming a full-time musician any time soon.
“No matter what level you pursue it at, there’s always a little bit of a battle to not feel like you’re being too selfish, because there are moments where you have to lock everything out and really get into that mode where you’re creating… and it isn’t always the most easy on those around you,” he said.
Pearsall added that he is in a good place at the moment and would not change anything.
“If somehow, I, by some bizarre chance, ended up viral somehow, and I’m booked to play in the whole world maybe then things would change. But until that day, honestly, I really like where I am right now … I’m really in a great place, I wouldn’t change anything,” Pearsall said.
For more information about Roland Pearsall, visit his website or his Instagram @rolandpearsallmusic, where he will be announcing future performance locations. His most recent album “Sell Your Soul” is now available on Spotify.