Rob Carlson: From Westport To Benefit Street, And Back

In a society that celebrates specialization, Rob Carlson is a generalist.

He’s a singer-songwriter. A corporate entertainer. An author. And a lot more.

Rob Carlson

Rob Carlson

For over 50 years — even before his 1966 graduation from Staples High School — Carlson has entertained generations of fans. He’s funny and fun. He’s got a wicked eye for the absurd, and a Robin Williams-like talent for picking out a wide range of targets.

Staples played a seminal role in Carlson’s musical career. As president of Orphenians, he helped organize the elite a cappella group’s 1st-ever trip (to the Virgin Islands).

He played trombone (“a useless instrument”), but discovered guitar (“you can actually play chords”). His folk band — the Triumvirate — opened for some of the famous rock bands like the Beau Brummels and Remains who played at Staples.

At Brown University — where he majored in American Civilization — Carlson was part of a burgeoning music scene. His most famous band — Benefit Street — included Staples classmate Josh Barrett. They earned New England renown.

In 1973 Carlson joined another former Staples classmate, Jon Gailmor, in a folk duo. Their Polydor debut album — “Peaceable Kingdom” — is still considered a classic by all who heard it.

But before hitting the big time, the 2 went their separate ways. Carlson headed back to the Virgin Islands, where he fell in love with Caribbean music.

Back in this area, he had a 10-year run playing local spots like  Grassroots and the Tin Whistle.

When his son was born — and Grassroots closed — Carlson got a steady gig running an independent production company. As “Ramblin’ Bob,” he wrote and produced a weekly tune in the style and voice of Bob Dylan, about whatever was happening in the news. The delivery was dead-on.

Christine Lavin heard Carlson in Portland, Maine, and gave his career a boost. He formed the Modern Man trio, which perfected send-ups of songs by the Beach Boys, Chuck Berry and many others. After 15 years, Modern Man played its last gig in October.

Carlson describes his music — reluctantly, because he dislikes categorizing it — as “folk/rock/Americana.” It includes elements of show tunes, R&B, Caribbean — you name it.

He’s “pretty much acoustic. I like the sound of wood.”

Benefit Street has now been reconstituted — with former Westporter Beth Bradley. This month they play the Grange in Greenfield Hill. On November 12, they and Beth Bradley will be at the Westport Unitarian Church’s Voices Cafe.

Palatine Ship - Rob CarlsonBefitting an American Civilization major, Carlson spent 30 years — “on and off,” he clarifies — researching and writing “Palatine Ship,” about the legend of an 18th-century vessel lost near Block Island.

But it’s music for which Carlson is best known. His audience, he says, is “mostly boomers. Every generation is fixated on the music it liked between the ages of 13 and 25. That’s pretty much what you like for the rest of your life.”

It’s a life Rob Carlson has known — and embraced — for over half a century. Westporters have long loved his distinctive voice.

It’s a good thing he gave up that useless trombone.

(For Rob Carlson’s website, click here.) 

8 responses to “Rob Carlson: From Westport To Benefit Street, And Back

  1. Rob and his band are up next at Voices Cafe on Sat. Nov. 12th – http://www.vociescafe.org

  2. Dan,

    The Orphenians brought home a steel-drum set (a gift from the local government, I believe) as a souvenir of the Virgin Islands trip in 1966. They resided in back of the Choral Rehearsal Room for my entire stint at Staples, though I do not recall anyone learning to play them. Does anyone know what became of them? Are they still there? — Scott.

  3. Ron and Jon played at Staples 50th reunion in July. Fantastic.
    Nice column, Dan.

  4. Nancy Powers Conklin

    Love Rob Carlson and his music! Followed him quite a bit when we lived in Fairfield fulltime.

  5. An honor to have shared some wonderful music and times together Rob… you have a special gift! Peace, Steve

  6. Have been a big fan from back in the Grass Roots days. We were there almost every Thursday night!!