Today we’d like to introduce you to Chuck McDermott.
Thanks for sharing your story with us Chuck. So, let’s start at the beginning and we can move on from there.
My musical life began when I was nine years old, after begging for a year for a guitar. We lived in Dubuque, Iowa and my sensible parents eventually relented and rented one for me and signed me up for lessons at the town’s one music store. They wanted to be sure I’d “stick with it”. I stuck with it. I’ve never put it down. I cut my teeth on folks songs by the Weavers and The Kingston Trio.
I was 13 when the Beatles hit and like every kid who knew three chords I formed a band and learned “When I Saw Her Standing There.” That led to more and more serious bands through high school. In college, I played coffee houses in New England and landed a summer-long gig in Aspen, Colorado after my freshman year which hardened my resolve to make music my life.
I limped through my sophomore year, mostly locked in my dorm room hunched over my guitar and dropped out by the end of that school year. I played music for a living for the next 14 years. The first decade of that was here in Boston. I began like most with a band doing covers of the day’s hits – songs by Crosby, Still, and Nash, Poco, The Byrds.
But I began to gravitate toward hard-core country music – Hank Williams, early Merle Haggard, Tammy Wynnette, Waylon Jennings, Willie Nelson. I steered my band, Chuck McDermott and Wheatstraw, hard in that direction. That move left some of my friends scratching their heads, but I was just in love with it. And there was work to be had for a country band.
There was a circuit around New England of clubs like Boston’s Hillbilly Ranch that would book you for two weeks at a time, six nights a week, five sets a night. We’d go from that to playing colleges and the rock bars in Cambridge. Country music became increasingly popular among the college crowd and even New York City got the “country bug”.
We were regulars at the now legendary Lone Star Cafe in Manhattan where stars like Willie Nelson and Feddy Fender would join us onstage and where the audience was littered with patrons like John Belushi, Kurt Vonnegut, Andy Warhol, Dennis Hopper. We put out two albums of primarily my material, got some encouraging critical acclaim from Rolling Stone, The Village Voice, The New York Times and others.
But we never got that Nashville recording contract. Something about being a long-haired, Yale-dropout, country singer from Boston that gave the Nashville folks some pause. So, about ten years into this journey, I decided to try a different angle. I accepted an offer to record for a new record company that was being launched based in LA.
I moved out there and soon learned that the “launch” wasn’t going to happen. This is a story known to many an aspiring musician! But it provided a fresh start. I started a new band that began to rise up in the crowded music scene there and feverishly wrote songs.
And it was there that I had the incredible good fortune to meet, befriend and ultimately partner with one of the Founding Father’s of Americana music, the late John Stewart. John remains one of the great American songwriters of his generation and it was a masterclass to record and tour with him.
Better still was the friendship we shared until his passing 10 years ago. After about 4 years in LA, I was now married and expecting our first child. While on the one hand, I was now sharing the stage and studio with heroes like Linda Ronstadt, Lindsay Buckingham, Bonnie Raitt and others, I took my new parental responsibilities seriously.
A friend was starting up a non-profit company in the energy sector and was staffing up. That brought me and my young family back east and it began what has been a 30+ year juggernaut that has included time in an energy trading start-up, a stint has a staffer in the US House of Representatives, an environmental advocate in DC and for the last 20 years venture capital investor in the cleantech space.
But through all that, I never stopped writing and playing music. And with my “day job” largely behind me, I’ve turned back to music full time. I released a record, “Gin & Rosewater”, last year and am touring around the US until they won’t let me do this anymore.
Has it been a smooth road?
No career in the arts is a smooth road. The potholes include long-duration extreme poverty, artistic rejection, long hours and a poor ecosystem of outside support. In my case, I was fine with being broke for the first several years but it can be defeating after a while. It makes almost everything a crisis and that’s fatiguing. And the arts aren’t necessarily a meritocracy.
In order to be “successful” which I defined for myself as being able to make a living wage playing my own music, you have to reach a certain level of proficiency. But even beyond that, anyone who has been at it will tell you that good luck and timing can make the difference between being stuck in a perpetual rut or achieving escape velocity that gets you to the next level.
And a career that involves working night hours and enduring lots of travel is at odds with a traditional family life for many. But all that being said, there are few things in life as satisfying as a great gig, when you feel you’ve connected with people who have come to hear your music, played by musicians your respect and enjoy. You don’t experience that in many professions.
We’d love to hear more about your music.
I describe my music as “Americana”, which is a Venn diagram that includes country, folk, blues – all forms of roots music. Strains of country music still run through my writing and instrumentation but I’ve opened the aperture to allow in more diverse rhythms, themes and ideas.
I’m primarily a story-teller as a songwriter. And I’m really enjoying the writing process at this stage in my life. I just have a lot more living under my belt than when I was in my 20’s. I’ve raised a family, I’ve said the final farewell to both my parents and some of my best friends. I’ve worked on issues of environmental protection and social justice with commitment.
I’ve been through a divorce, then found deep love later in life. Through it all, (with certain exceptions) I don’t see the world in black and white terms. I see light within the dark and sometimes dark inside the light. All this means there’s a lot to write about!
Let’s touch on your thoughts about our city – what do you like the most and least?
Boston has a personality. There’s an overarching personality that is shaped by its place in our country’s origin story, the ever-present antiquity and sense of history.
Then, the individual neighborhoods have their own distinct personalities – some gritty, some tony, some academic, some athletic. Being a coastal city adds a lot the quality of life here – I can commute to and from the city from my home on the south shore by BOAT!
In the “room of improvement” category, I’d point to the T. Let us no longer defer the deferred maintenance!
Contact Info:
- Website: www.chuckmcdermott.com
- Email: chuckmcdermottmusic@gmail.com

Image Credit:
Kelly Davidson Studio
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Barry Glovsky
November 17, 2018 at 11:00 pm
Chuck defines dedication and persaverance to his art. his sound is quite unique and his time is coming.
D.W. George
November 19, 2018 at 7:43 am
Amazing singer/songwriter! I got Chuck Mcdermott’s Gin and Rosewater CD and now on a Spotify playlist. Seriously brilliant.