Boston Street Busker Weathers through All Seasons to Perform

Caleb Hensinger, who has been a busker in Boston since 2015, performs in Copley Square on Saturday, January 27, 2018. Photo by Ying Wang/ BU News Service.

By Ying Wang
BU News Service 

Scores of protesters gathered at Copley Square, about 30 feet from where Caleb Hensinger usually performs. Hensinger decided to wait, as he didn’t want them to think his performance was meant to oppose to their protest.

It was a calm and mild Saturday in January. High sunlit clouds drifted across a clear blue sky. Hensinger is one of the street buskers who choose to stay in Boston in winter. This particularly warm day allowed him to discard hand warmers and the plastic bags that he usually puts over his socks. He set up his keyboard, speakers and a 5-gallon bucket as he prepared to perform.

“It’s gonna be good business,” Hensinger said.

The 25-year old, blue-eyed and bearded California native has been performing on streets in Boston since graduating from the Berklee College of Music in 2015.

While the busker was setting up his 3-foot-tall speaker and unfolding a bunch of cords kept in sandwich bags, another elderly busker walked by with his red hand truck.

Street performers can typically occupy prime busking spots at the same time. Common areas include Downtown Crossing, Quincy Market and Copley Square. Hensinger said that it is important for them to socialize with others, as well as the homeless living on streets.

“I make sure that [the homeless] know that I’m not there trying to take anything from them, but to play some music, ” Hensinger said. “They can see that they can get more money when I’m out there.” The busker added that giving away some food or a dollar bill is considered proper etiquette.

Hensinger pressed down upon the pedal of his instrument and began to play Stevie Wonder’s “Superstition.” Passersby went about their business in the square. Two men in suits strolled by with coffee while a skateboarder sang along. A dozen groomsmen and bridesmaids stopped to dance. Their white hydrangea bouquets bounced to the beat.

As the rhythm progressed, Hensinger began to sing through a slim rubber tube connected to the keyboard. The song changed to Bruno Mars’s “Treasure.” Hensinger picked up his rusted trumpet that was given to him as a gift by his grandma, stepped onto his wooden stool and swayed to the music.  

In 10 minutes, seven audience members took out a few dollar bills and walked toward the blue bucket that Hensinger carries all the time — even when going to the bathroom.

Usually though, Hensinger doesn’t use the restroom for hours. He performs alone, and there is no break.

It’s the same with water. He drinks a ton of it before going to the gym at nine in the morning, and that’s the only water he has all day.

His friends were astonished by how he drank water after his performance.

“I don’t even taste or feel the water. It’s just absorbed by my throat,” Hensinger said. “ After three glasses, I finally feel my stomach.”

The Boston winters are tough for street performers.

“Everything is kinda huddled together in winter. Wearing heavy jackets is more exertion,” Hensinger said.

Some buskers drink alcohol or bring blankets to keep warm, but Hensinger doesn’t find this necessary.

He has come to recognize people who come see him play regardless of the season.

“I treat winter audiences as long-term clients,” he said.  

A number of buskers from all over the world come to Boston in the summer, and many of those based in Boston choose to move to warmer areas like Florida in winter, according to Stephen Baird, a busker who started his career playing music on the streets in 1972. He is also the founder of Street Arts and Buskers Advocates, a non-profit aiming to expand public support of street performance in Boston.

“The jugglers and magicians that combine major visual action do a lot more tours in migrating to warmer climate,” said Baird. “They come out once in a while in Harvard Square or Faneuil Hall, but most of them really make their living off the vacation crowds.”

Chadd Deitz, a stunt comedian, is one of them. Originally from Syracuse, New York, Chad moved to Massachusetts when he was 23 for his ex-girlfriend in 2009 and has been busking in Boston for six years. Besides performing for college shows, festivals and gigs, he regularly gets scheduled at Faneuil Hall, where he earns tips from the outdoor crowds.

“My schedule does get pretty busy by spring, summer and fall,” Deitz said. “It can be up to three shows a day and three days a week.”

Deitz attended the World Buskers Festival in New Zealand last January and just won $3,000 at the Annual Eustis Busker Festival in Florida in March. He will be returning to Boston this month

For other buskers who don’t migrate to perform, there is another solution to stay warm. Some may choose to perform inside train stations. There is no license required to perform on streets, but a permit costing $25 annually is required in train stations.

According to the MBTA Realty Group, there were 152 and 138 subway performer permits issued in 2016 and 2017, respectively.

But Hensinger still earns more outdoors than in train stations in winter.

“You are like a nuisance in train stations,” Hensinger said. “It’d be better to be quiet for people with headphones.”

What Hensinger likes most about busking is that performers don’t have to be perfect.

“I want performers of different levels to be there, because that means our country values the fact that we have all sorts of opinions being spoken,” he said.

Busking requires long hours and not the best pay, yet Hensinger doesn’t seem to want to quit.   

“The worst days are always like [just] 10 dollars, but the potential is that you could make thousands a week by selling albums to people that walk by and talking to them in a way that demands they have empathy for your situation,” he said.

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