KING SIZE TALENT: Charlie Chesterman, Scruffy Sweetheart of The Rodeo

Charlie's thirsty after (or is that before?) the gig with Scruffy The Cat, somewhere in the '80s

Charlie’s thirsty after (or is that before?) the gig with Scruffy The Cat, somewhere in the ’80s. Big thanks to Wayne Valdez for taking and furnishing the pictures that appear on this page (with the exception of the Scruffy publicity shot). Wayne had helpfully sent me these to run as a photo slideshow with my Globe feature in 2011 and I greatly appreciate his having the foresight back then to document these moments in the band’s life and share them with us.

Roughing it outdoors, Scruffy style.

Roughing it outdoors, Scruffy style.

Scruffy The Cat, ready for their close-up

Scruffy The Cat, ready for their close-up

Studio portrait of Boston roots-rock band Scruffy The Cat. L to R: Mac Paul Stanfield (bass), Randall Lee Gibson (drums), Stephen Fredette (guitar), Charlie Chesterman (guitar/vocals), Stona Fitch (banjo, organ, accordion)

Studio portrait of Boston roots-rock band Scruffy The Cat. L to R: Mac Paul Stanfield (bass), Randall Lee Gibson (drums), Stephen Fredette (guitar), Charlie Chesterman (guitar/vocals), Stona Fitch (banjo, organ, accordion)


Scruffy The Cat Cowboys at the Rock & Roll Rodeo

Scruffy amid the scrawl: The Cat cuddles up in clubland.

Scruffy amid the scrawl: The Cat cuddles up in clubland.

Besides his exuberant rock & roll music — and he made a lot of it, thankfully for us, over the years — his easy laugh is what I most identified with Charlie Chesterman.  The Iowa transplant who moved to Boston and made his mark as one of the city’s most beloved singer-songwriters, first with the essential local ’80s outfit Scruffy The Cat and then with a grab bag of other equally fun, rocking, and rootsy bands, lost his long, valiant battle with colon cancer yesterday. But not without picking up his guitar a few times more to play, even after he got the bad news. And not without keeping his easygoing grace, undiluted rock & roll spirit, and that quick, affable sense of humor.

I had the pleasure and privilege of interviewing Charlie twice for features in The Boston Phoenix (Charlie was one of my chosen subjects for the Phoenix’s long-running “Cellars By Starlight” local music column), and then, eleven years later, for The Boston Globe, after he had gotten sick. The Phoenix piece marked the occasion of a cool Chesterman solo album, “Ham Radio.” The premise of the second interview, I thought at the time when I rang him up, was going to be a much harder conversation about a much tougher subject: not the celebratory release of a new record, but rather the effort being undertaken by his many musical friends, to raise money for his care and medical bills. It was not going to be an easy interview — for either him or me. Or so I thought.

Charlie picked up the phone, offered a warm, spirited hello, and sounded immediately like his old self.  And then both of us picked up where we had left off a decade earlier, when we ate and mulled over music at the now long gone Deli Haus diner in Boston’s Kenmore Square. It only occurred to me later that I had opened both of my pieces, despite the dramatically different circumstances, with references to that infectious laugh of his. And just now while listening to Charlie’s upbeat little ditty, “I Hate Everything,” from an excellent new compilation put together by his close friend and producer, Pete Weiss (see link to listen and order below), it occurs to me that I’ve done it again. You know what? I think I’ll leave my lead as is. Because Charlie would have probably gotten a chuckle out of that.

Here’s  both my original “director’s cut” full-length feature on the Scruffy reunion fundraiser from 2011 (somewhat longer than the piece that was published in the Globe), and the Boston Phoenix feature from 2000; I’d like to think of this page as my version of what passes for a prayer (Mona’s and otherwise) for, and tribute to you, Charlie.  Hope these stories did as right by you as your wonderful music does by me, every time.

Ask Charlie Chesterman how it feels to be the guest of honor at a star-studded benefit being organized to raise money for his battle with colon cancer, and he responds with a boisterous cackle. “That’s my answer – laughter is my answer,” an amiable and upbeat Chesterman says over the phone from his Dorchester home. “I’m actually feeling OK at the moment.  Sometimes I’ve got shitty days and shitty weeks, and sometimes I’m kinda up. Right now I’m kinda up, so that’s good.”

Chesterman, 51, a singer-songwriter who’s been undergoing chemotherapy since being diagnosed last year is, of course, best known around these parts as the former frontman for Scruffy The Cat, an ‘80s roots-rock outfit from Boston that played as hard as it worked. With its raucous live shows and maverick spirit cut with a reverence for tradition, Scruffy helped spark what would come to be called the underground “cowpunk” or “alt-country” movements of the late ‘80s and early ‘90s.

“There would be no Wilco without Scruffy The Cat, because of that hybrid [they brought] of rock and roll with a punk edge,” says benefit organizer John Fremer, a guitarist who played with Chesterman in his post-Scruffy band, the Harmony Rockets. “It’s not really hyperbole to say that a lot of the alt-country scene wouldn’t exist without them. I learned so much from Charlie as a songwriter, and as a rock and roll spirit, I’d put him up there with Iggy Pop and Joan Jett; singular people who are very unique characters who embody rock and roll.”

This Sunday, a who’s who of local luminaries will take the stage at T.T. the Bear’s for a day-long tribute to Chesterman and his music. And for the first time since they disbanded more than 20 years ago, Scruffy The Cat are set to reunite for what band members promise will be a mini-set of seat-of-the-pants surprises.

“We’re going to get up there and wing it,” says Scruffy drummer Randall Gibson, who’ll join Chesterman and Scruffy alums Stephen Fredette (guitar), and Burns Stanfield (keyboards) on stage. Stanfield, an ordained minister, will head to T.T.’s straight from Church. “What I said to Charlie was, it’s going to be fluid,” Gibson says. “He got a real hoot out of that. But we toured so heavily and played so many shows – sometimes, we’d play (multiple sets at multiple clubs) four or five nights a week – that I think we’ll remember the songs. We probably played them a couple thousand times.”

Even though the principals hesitate to call it a full-blown reunion – Scruffy bassist (and Burns’s brother) Mac Paul Stanfield can’t make it out from his home in Des Moines, Iowa (also Chesterman’s hometown); and banjo player Stona Fitch will be in New York celebrating his 20th wedding anniversary – it’s as close as anyone could, or would, ever expect given the circumstances. Besides his own serious health issues, Chesterman’s old guitar foil Fredette has struggled with lymphoma for several years (which, Fredette reports, has been in remission). Even Charlie’s surprised.

“Out of all of us, I think I’m the one that has been the biggest foot-dragger about getting back together,” says Chesterman, who’s recorded six solo albums, three of which were released on the Salem-based Rykodisc/Slow River label. “But between the health situation that Stephen has and I have, it’s kind of changed my perspective a little bit. I guess now’s as good a time as any. If everybody really wants to do this and I’m the only hold out, then I just need to shut up and get with the program. It’s time for me to just say yes.”

Plus, Chesterman says he feels “healthy enough” to take another stab at Scruffy staples like “My Baby, She’s Alright,” a tune that landed them on MTV back in 1987, around the time the group was sharing stages with the likes of the Replacements, Los Lobos, and – er – Paula Abdul (A Spin magazine anniversary party that, to this day, remains a “ghastly” memory for Fredette). “(Randall) mentioned to me the idea of trying to pick some mid-tempo songs because we’re all old guys now,” Chesterman says. “But I have a feeling when he gets behind the drum set it’s going to go a million miles an hour, whether he wants it to or not.

“I haven’t really been able to play guitar for a year or so … just because treatment and various things that made my hand kind of wacky, and I think that Stephen has been in a similar boat,” Chesterman says before suddenly brightening, as if arriving at the punch line of a preposterous joke. “So I think between the two guitar players, there’s going to be very little guitar playing going on! Maybe we’ll just hum or just shake maracas instead.”

You can practically hear Fredette also shaking his head over the phone. “We were supposed to do this a year or so ago, and that’s when I was sick,” Fredette says. “So I guess it does take a rather dire situation for it to happen.”  All the more reason to revel in Sunday’s semi-reunion, he says, and let the songs (the set list’s a secret) fly.

“Obviously, we weren’t a band that had a huge impact, and I think a lot of that had to do with the fact that a lot of the recorded stuff wasn’t as strong [as the performances],” Fredette says of Scruffy’s two albums and two EPs released on Relativity Records. “But live, it was like a bomb going off.”

“We left our mark,” Gibson says proudly. “We came in at just the right time when Boston bands were getting noticed, and that’s when roots rock was taking off. We were pigeonholed as a ‘cowpunk’ band because of the fact that we had a banjo and the guys liked to play Gretsch guitars and we had a few country-ish songs. But I never felt we were a ‘cowpunk’ band or anything like that at all. I just thought we were a rock and roll band.”

The formula for a Scruffy The Cat show was simple, says Gibson: “Leave all the depression and politics and anger at the door when you come to a Scruffy The Cat show, because you’re not going to find any of that there. What you’re going to find is songs about girls and beer. That’s what we were about. Everyone can have a bad time, in their life, all day long. But when you go to a nightclub, do you really want to pay ten bucks to go out and be depressed? (With us) you were guaranteed an hour and a half of high-speed, drunken fun. And we never let them down.”

“We were all in really good shape back then — which I don’t think any of us can claim to be anymore!” says Chesterman. “We worked really hard and played really hard. I was really, really fortunate to be involved with the guys who were in Scruffy. It might have been slightly dysfunctional, but we didn’t fight or quarrel or piss each other off too much.  At one point, we were a really, really tight band because of all this playing that we did. But we could all spend hours and hours in the van together and still be able to get up on stage and not want to kill each other. I think that’s the thing I come away thinking about. Being with a bunch of guys that I really liked, and really liked playing with.”

“In the grand scheme of things, I don’t know where Scruffy fit in,” Chesterman muses. “But it is amazing to still, every once in awhile, get an e-mail from a fan saying, ‘I was listening to your record the other day and you guys were a great band.’  We had a really good time and people connected with it that way.”

Longtime Chesterman producer Pete Weiss recalls Scruffy as “an astounding live band, and they rehearsed heroically. Doing that, you have no choice but to become this incredibly well-oiled machine. And on top of that, you had the great songwriting, great hooks, and the guitar heroics of Stephen Fredette — that’s something in and of itself.” Scruffy’s range, Weiss marvels, went way beyond one narrow style or genre catchphrase. “They weren’t just influenced by punk or twang. They could lay down a nice little dance groove, as necessary.”

In fact, as traditionalist a rock & roller as he could be, Chesterman’s broad range of songwriting styles and moods becomes quickly apparent when you listen across the spectrum of his post-Scruffy solo stuff — a body of work that Weiss hopes will return to the public ear soon. The producer, who now operates his own Verdant recording studio in Vermont, has been poring over tapes and prepping the songwriter’s solo material for digital release (efforts are also underway to obtain the rights to Scruffy’s catalog, which has long been out of print). He recalls feeling an instant musical kinship when, as a young engineer and producer, he first met Chesterman at Zippah Studios in Brookline.

“I was always happy to indulge Charlie in his hair-brained schemes, such as recording his vocals in the backseat of a car” – Weiss’s 1982 Buick Skylark nicknamed “Grampy”, in fact – “which doesn’t necessarily sound good, but creates an intimacy,” Weiss says. “Or he’d bring in a 55-gallon drum and say, ‘Hey, let’s make an echo chamber out of it!’  He’s got amazing ideas, he’s got wacky ideas,  he’s got weird schemes. And he’s happy to shoot himself in the foot occasionally in the interest of art.”

“We were in the same room for 22 years,” says Fredette. “Meeting Charlie was the first time I was exposed to a really great songwriter. And on top of it, as a frontman, you didn’t ever have to worry about feeling like you were compromising yourself, because Charlie’s obviously very natural, so ‘show business’ elements didn’t enter into it. Coming from a punk rock background, it mattered. It would have felt horrible to feel false. And it was never an issue. It worked as music and a show and entertainment without stooping to anything.”

Chesterman may not be done with making music just yet. He’s got some songs he’d still like to record, and depending on how things go Sunday, future Scruffy shows with all members present haven’t been ruled out.  A short time ago, he never thought he’d play again.

“It was easier for me to devoid myself of that part of my life and concentrate on trying to get better,” says Chesterman. “So this whole show that’s coming up was out of  left-field for me.  But to have it all come together, it’s  like, yeah that’s right. I do play music, and I can play music if I want to. Maybe that’s what I should be doing again.”

HAM RADIO ON WRY (Originally published in The Boston Phoenix, Nov. 23-30, 2000)


Charlie Chesterman laughs loud, early, and often. Over a meatloaf sandwich at the Deli Haus in Kenmore Square, Chesterman’s decribing the worst-case scenario surrounding his decision to release his new album, Ham Radio, on his own Aerola Recordings label. “I may find out this time next year that the people I think are out there and interested in what I do aren’t really out there, and I’ve got a basement full of records.” He punctuates the picture he’s just painted with a wheezing guffaw that escalates into an almost hysterical cackle.

Chesterman’s chuckle usually comes when he tries to assess his staying power as a musician on a local music scene that’s turned over hundreds of faces since he left his hometown of Des Moines, Iowa and landed in Boston with his band, the Law, in 1981. Chesterman’s best known, of course, for his mid-’80’s indie roots-pop outfit, Scruffy the Cat. But he’s never stopped writing and performing before or after his Scruffy days — with or without his band the Legendary Motorbikes.

“I’m really very thankful about that, because I’m trying to think of people who would’ve been around at the same time Scruffy got started who are still plugging away and most of these people don’t do it anymore,” he says. “Part of it is playing with a really good band … that’s what keeps me going  I’d like to say I’m talented, but I have a little knack for a melody and then after that it’s all luck. Along with being fortunate enough to have a history and background that pretty much whatever I’ve done as a musician has always been accepted. That’s not a brag, that’s just — I’m fascinated by it because I don’t understand it.”

Industry bigwigs may have their reservations about Chesterman — he’s no longer affiliated with Slow River/Rykodisc, the Salem-based label that put out each of his last three albums before its merger with Palm — but listeners who still like their rock & roll served neat, with toasts to old masters like Buddy Holly and Chuck Berry, are plagued by no such doubts.  And perhaps because it’s been three years since Chesterman’s last release, *Dynamite Music Machine* (Slow River/Rykodisc), Ham Radio sounds like a particularly fresh, long overdue blast of tang ‘n’ twang. It’s an album lousy with scrappy licks and scruffy hooks, and not one ballad in the lot.

“I really wanted to put out another record because I felt like I had the material and the band was playing really well,” Chesterman says of his gamble to “sink or swim” by releasing Ham Radio on his own. “(Dynamite Music Machine) didn’t do as well as (Ryko) thought and along comes the merger with Palm and I kind of got lost in the shuffle and then it was free-agent time. But what’s the point of belly-aching? I’ve had it happen before, when the label doesn’t help out anymore and you don’t know what to do and then the band breaks up and then you’re just screwed. It can get the best of people and there’s no reason to have that happen now. Why give up just because somebody else isn’t going to help?”

Far from giving up, Chesterman talks like a guy who’s just getting started. Next year, he’s  toying with the idea of releasing a downloadable, Internet-only Harmony Rockets album (a collection of short, fast songs named after his short-lived early ‘90’s band) on his new website (; putting out a live album with the Motorbikes; and recording a stripped-down solo album of just voice and guitar. At some point, Chesterman also very much wants to take a stab at making a “very, very beautiful pop record” with strings and horns, just because it’s something he’s never done.

For now, Ham Radio is sure to continue Chesterman’s 20-year lucky streak with audiences who haven’t stopped caring. The disc wears as comfortably as a favorite demin shirt, and easily lives up to its advance album-cover billing as “delicious and electric.” With Chesterman’s easy-going voice out front — nearly a dead ringer for Silos singer  Walter Salas-Humara’s — Ham Radio is a raucous collection of cheeky numbers with lost era-evoking names like “Mustang Twang” and “Crickets Love Song” (the latter’s an instrumental homage to Buddy Holly’s backing band). The rockabilly-flavored opener, “When I’ve Got Me (And All I Want Is You)”, sets the pace right off the bat: it’s a 2-minute-21-second freight train pulled along the tracks by Chesterman’s and Andy Pastore’s grimy, coal-shoveling guitars. Meanwhile, the crack rhythm section of bassist Jim Faris and drummer Gary Gendron basically never stops chugging.

“We wanted to keep that (Dynamite Music Machine) feel without having to stay up really late and drink a lot of coffee and beer,” Chesterman explains. “And we also wanted to try to make it sound better — not to make it slicker and more polished, but just to present it as a cleaner whole. Spend a little more time with the material.”

Ultimately, Ham Radio is an extension of  the music Chesterman’s loved since his junior high school days growing up in Des Moines, playing guitar in a ‘50s cover band (” a third-rate version of Sha-Na-Na”).  It’s high spirited and “uninfected”, as the London Sunday Times once put it, “by the postmodern irony virus.”  Chesterman giggles at the quote. “I’d like to think that everybody thinks that rock & roll’s fun, or that rock & roll can still be fun. But I look around and I don’t see it as much as I wish I did.  And maybe I’m not looking around in the right places. But (my music) is not necessarily a reaction to anything as much as it’s, well, trying to be honest.” With that approach, you can bet that Chesterman will have the last laugh yet.

Listen to (and by all means pick up) “Solid Gold Electric Chestnut Dispenser,” the terrific new compilation of rare cuts and more here:

Here’s a link to my Boston Globe piece, originally published online here:

Here’s a link to my Boston Phoenix “Cellars By Starlight” piece on Charlie (and The Heygoods, also profiled) originally published here:

Finally, here is an obituary and biography written and put together by Charlie’s family and friends and released to the press:
Boston rock musician Charlie Chesterman died Monday after a long illness. He was 53.
Born and raised in Des Moines, Charlie was lead singer of The Law, one of Iowa’s first punk bands, in the late 1970’s. He moved to Boston in the early 1980s where he started Scruffy the Cat, writing songs, playing guitar and singing most lead vocals. The band was at the forefront of a budding roots-rock movement, touring the U.S. relentlessly, sharing bills with the likes of The Replacements, Yo La Tengo, and Los Lobos, while releasing two full-length albums and two EPs on Relativity Records. After garnering attention on Coyote Records’ 1986 Luxury Condos compilation, Scruffy the Cat’s first EP High Octane Revival earned the fourth spot on the Village Voice 1986 Jazz and Pop Critics Poll. The band’s debut full-length album Tiny Days was released the following year and quickly topped college radio playlists. The video for the album’s track “My Baby, She’s Alright” entered rotation on MTV and the band was later profiled in Newsweek magazine. During an interview conducted from a street corner phone booth, Charlie commented on Scruffy the Cat’s spread in Rolling Stone‘s “Back to School” fall fashion issue, “We were going to get into Rolling Stone one way or another, so we figured we might as well get pictures of us with someone else’s clothes on.”
In 1988, a follow up album was recorded in Memphis with famed producer Jim Dickinson. Although Moons of Jupiter was not as enthusiastically received in pop circles as the previous album, the experience of recording in the shadow of Elvis, Al Green, Booker T and Stax/Volt left a deep impression on Charlie. It proved pivotal in leveraging both his own development as a crafter of songs and in his transition from pop star to mature artist in the wake of Scruffy’s subsequent disbandment. As Chris Heim observed in a glowing 1988 Chicago Tribune review of the album: “It wasn’t quite as dramatic as Saul on the road to Damascus, but something did happen to the Boston-based band Scruffy the Cat on its way to Memphis that converted once punky attack cats into sweet, soulfully cool kitties.”
In the early 1990s, Charlie formed The Harmony Rockets, a jangly, British-pop-rock-influenced band. Popular and critically-acclaimed, the band played around the New England region, and released one record. In 1993, he recorded a few demos as a solo artist that resulted in his signing to Slow River/Rykodisc Records, with whom he recorded three albums — From the Book of FlamesStudebakersfield, and Dynamite Music Machine — that formed a sort of tragedy-to-redemption trilogy. He later put out three more albums with his band The Legendary Motorbikes, often known simply as Chaz & the Motorbikes.  After stepping away from music for a few years to focus on raising his family, he issued a collection of unreleased and rare recordings entitled Solid Gold Electric Chestnut Dispenser.
Charlie’s longtime producer Pete Weiss said, “I feel incredibly lucky to have had him as a close friend and collaborator. And I’m very grateful to have been invited into his amazing musical world. I love, love, love how uncompromising he was with his music, and how he looked at rock and roll through a visual/conceptual artist’s lens.”
Charlie loved Rickenbacker guitars, motorcycles and Vespa scooters, and collected mid-century American graphics.  He studied and cherished the songwriting finesse of Buddy Holly, the raw grit and creativity of the early Beatles, the bombast of Little Richard, the twang of Eddie Cochran and Gene Vincent, and the ageless pop-rock of Chuck Berry, all of whom factored into his own style of songwriting and performance.  In addition to his musical career, Charlie worked for many years at Boston’s PSG Framing.
Charlie died peacefully at home surrounded by family. He is survived by his wife Juliann Cydylo, his daughter Clementine and son Woolsey, his sister Nancy Covington, his brothers Ted and Dan Austin, and his mother Carolyn Chesterman.


  1. Your style is unique compared to other people I’ve read
    stuff from. Thank you for posting when you have the opportunity, Guess I will just bookmark
    this page.


  2. Reblogged this on RPM: Jonathan Perry's Life in Analog and commented:

    Thinking about singer-songwriter-musician-showman Charlie Chesterman today on the second anniversary of his far too-soon passing. I had the good fortune to interview Charlie and write about the music he made with his many outfits and combos over the years, including Scruffy The Cat, the Harmony Rockets, Chaz & The Motorbikes, and more. The Des Moines-born musician’s tenure during the late ’70s as lead singer for The Law, one of Iowa’s first punk bands (!), pre-dated me. But I wasn’t at all surprised when, after his passing, somebody played me a rarer-than-rare Law 45 single and it was damn good, filling up the room with his vivacious, electric spirit. Pretty much everything Charlie touched musically had both a crackling immediacy and casually sneaky staying power. If only Charlie had the same knack for sticking around longer than he was able to.


  3. A beautiful and touching tribute to Charlie, one of my all-time favorite people.


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