In Boston’s thriving rock ’n’ roll scene of the 1980s, Charlie Chesterman’s dynamic performances as a singer and guitarist with the roots-rocking Scruffy the Cat were legendary as he helped guide the band each year through 250 to 300 shows, many of them in area clubs such as the Rat, T.T. the Bear’s, the Channel, and Jonathan Swift’s.
“He was born to write songs and perform them,” said Burns Stanfield, who grew up with Mr. Chesterman in Des Moines before following him to Boston to join Scruffy the Cat. “He tapped into this joy and he took the rest of us along for the ride.”
The band’s first album, 1987’s “Tiny Days,” was ranked No. 4 in the Village Voice’s poll of critics and made Rolling Stone magazine’s list of Top 10 college records. All the attention left the likable, happy-go-lucky Mr. Chesterman bemused, at least in retrospect. “In the grand scheme of things, I don’t know where Scruffy fit in,” he told the Globe two years ago, adding that “We had a really good time and people connected with it that way.”
Mr. Chesterman, who was known for leading the band through high-energy, marathon performances, died of colon cancer Nov. 4 in his Dorchester home. He was 53.
“In Baltimore, we played a two-and-a-half hour set,” said Stephen Fredette, a guitarist who founded Scruffy the Cat with Mr. Chesterman, “and when we went back to Baltimore, the club owner put the opening acts on very early so we could play another two-and-a-half hour set.”
Mr. Chesterman, who came to Boston after hearing about the vitality of the music scene, turned Scruffy the Cat shows into joyous affairs and would do anything to rev up a crowd. Once he removed a shoe and placed it on his head during a WBCN Rock ’n’ Roll Rumble show, then tossed it into the audience and played the rest of the set wearing one shoe.
Admired by many for his effortless sense of what was cool, Mr. Chesterman loved Rickenbacker guitars, Vespa scooters, and vintage sweaters. Among the musicians he admired, his holy trinity was Chuck Berry, Hank Williams, and the Ramones, and he was thrilled when Joey Ramone saw Scruffy the Cat perform at the Ritz in New York.
“Charlie was always happy,” said his older brother, Ted Austin of Des Moines. “He enjoyed whatever was around him. And he never took a music lesson.” Mr. Chesterman did become an Eagle Scout, his brother added.
Starting out in Des Moines by playing in the Flashbacks, a 1950s cover band, Charles E. Chesterman went on to form the Law, a band he brought to Boston in the early 1980s before founding Scruffy the Cat.
For Relativity Records, Scruffy the Cat recorded two full-length albums, “Tiny Days” and “Moons of Jupiter.” The band also recorded two EPs, “High Octane Revival” and “Boom Boom Boom Bingo.”
The band broke up in 1991, partly from the exhaustion of touring so often while traveling great distances. Scruffy the Cat would perform across the country and then go into Western Canada, while sometimes sharing tours with bands such as the Replacements, Yo La Tengo, and Los Lobos.
After Scruffy the Cat, Mr. Chesterman formed the Harmony Rockets and Charlie Chesterman & the Legendary Motorbikes, recording six more albums in the process, three of them for Slow River/Rykodisc Records.
“For me, it all started with Charlie’s voice,” said George Howard, who owned Slow River at the time. “He doesn’t always sing on key, but it’s one of the most distinctive voices you’ll hear. He doesn’t sound like anyone else.”
He always recorded on his own terms and “never sold out,” said Pete Weiss, his longtime producer at Zippah studios in Brighton. “He stuck to his guns.”
As was the case during live shows, Mr. Chesterman was prone to spontaneity while recording. He once tried singing in a cardboard box for a song about being boxed in. Another time, he wanted a microphone placed in the middle of the floor while his drummer rode circles on a bicycle, sounding its bell for added effects.
“He also had a knack for writing songs that were very simple and would nestle into your brain,” Weiss said, “but if you pulled them apart they were more complex than they seemed.”
Above all, Mr. Chesterman had an electric stage presence. His sister, Nancy Covington of Des Moines, recalled seeing him play at his middle school in Des Moines “and the girls were screaming. I knew he had found something he wanted to do.”
Mr. Chesterman’s wife, the artist Juliann Cydylo, said his immense will to live kept him alive longer than expected.
“Charlie was stubborn,” she said. “He lived two and a half years longer than the doctors thought. He was in bed since June, but we would listen to music together.”
She added that “being with him was an extraordinary experience right until the end. He was a gentle soul, and very romantic.”
Michael Charles, one of Mr. Chesterman’s best friends, said that “he never complained, even when he had cancer.”
Charles, who used to take long Vespa rides with his friend to Cape Cod and into New Hampshire, said Mr. Chesterman would “just say, ‘I’m going to the doctor. Let’s go.’ And that was it.”
A service has been held for Mr. Chesterman, who in addition to his wife, brother, and sister leaves two children, Clementine and Woolsey of Dorchester; his mother, Carolyn (Essington) Chesterman of Des Moines; and another brother, Dan Austin of Des Moines.
Two years ago, musicians held a fund-raiser at T.T. the Bear’s in Cambridge to help Mr. Chesterman pay his medical costs. Among the acts who took to the stage were Ray Mason, the Upper Crust, the Weisstronauts, Raging Teens, and Roy Sludge. Even Peter Wolf of the J. Geils Band showed up to sing.
In a phone interview with the Globe before the show, Mr. Chesterman was asked what it was like to be a guest of honor at such a benefit. A rocker who never quit, he let out a cackle and said, “That’s my answer — laughter is my answer.”
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