In 1971, Tom and I moved to Boston and started a group we called Wheatstraw. Like in our Aspen days, we played a little bit of everything and started to sprinkle in our own tunes. Though the first year was beyond lean, we began to get some traction on the college and club circuit in New England and eked out a living. In those early years, the band all lived in the same house and we pooled our gig money to pay bills and buy guitar strings and divided evenly what little was left over – if anything. 

 

One sanctioned expense was the occasional pilgrimage to the record store to buy new inspiration. A typical outing might bring home Johnny Otis live at the Monterey Pop Festival, a BB King Record, something by The Band, Loggins and Messina. I personally began growing restless with this “little bit of everything” approach. And around this time I became deeply attracted to Tammy Wynette’s classic “Stand By Your Man”. The piercing purity of her voice, the ache – it all profoundly touched me. So I made a list of country artists that I either admired already or thought I should admire because Gram Parsons’ records told me I should admire them! So on the next trip, I grabbed a Hank Williams greatest hits record, one from Tammy, a Merle Haggard record, and a double album by Bob Wills and the Texas Playboys. We brought those and our other purchases back to the band house, I fired up a bone, put on Hank Williams and was forever a changed man!

 

Those classic country records just seemed to fit like a glove. I felt that as a singer and performer I could span the distance between “Hey Good Lookin’” and “I’m So Lonesome I Could Cry”. The music of Hank and Ernest Tubb and others was not entirely foreign; those voices had come out of the radio at night when I was a child. The narrative songwriting style was only a step or two away from the folk songs I started out on, and I gravitated to their directness. I so doubled down. I was going to learn how to play, sing and write country music. I started by talking our way into a gig.

 

There was a local country roadhouse just down the street from where I lived outside of Boston that was the real deal. It was called the Turtle Lounge! And they had live bands 4 or 5 nights a week, all straight country. They all wore uniforms, sported pompadour hairdos. The very loyal audience of regulars kept the dance floor full. I was the only freak at the bar with hair down to my shoulders and a droopy red mustache.  But I managed to talk the owner into let us have a gig Wednesday night to see how things might go.

 

The rest of the band was not quite as enthusiastic about all this as I was. For one, we didn’t have uniforms. A couple of us didn’t have a second pair of Levi’s. But I got us each a black shirt, which checked the box.  Then there was repertoire – we didn’t know many country songs. I assured them that our knowledge of the Burrito Brothers’ songbook would get us through one night if we padded it with some rock tunes.

 

So we showed up for our big night. As we set up, you could tell that the audience had no idea what to make of us. We blasted through our first tune, stumbled through the ending to a smattering of light applause. I go into the next song – no one moves toward the dance floor. After that song, a fellow approaches the bandstand and hands me a cocktail napkin. It has scribbled upon it, “Play the Green Green Grass of Home”. I feigned a smile and said,” We can’t do that one right now but we’ll have it for you next week”, not at all sure there would be a next week. It pretty much went on like that through four tough sets. They did eventually start to dance – some of them. And I got a few laughs out of them from time to time. But two amazing things came out of it: we survived the night, and the owner decided there was something about us he liked and he said we should just keep showing up for Wednesday nights until further notice. I was dumbfounded.

 

But I kept all the napkins with song requests. I hit the record store and bought these “Country Hits of the 60’s” compilation records and just dug in. The next week we had about 20 new songs. The week after that another 20 more. We ended up playing the Turtle Lounge on and off for the next several years and several other “long haired country bands” followed us.

 

We still played our college gigs and rock bars on the weekends but my country music romance was causing rifts in the band. Two guys quit, my buddy Tom being one of them. I took that as an opportunity to hire the only hippie pedal steel player in a 50 mile radius. I got a cowboy hat. And more importantly, I stopped playing the rock stuff. We showed up and just did our country music, more and more of it my own. But we had a lot of youthful energy and we were determined to make our audiences see what we loved about it. And low and behold, it started to turn into a “thing” in New England.

 

It’s now 1973-74 and there are maybe three bands now like Wheatstraw – former rock’n’rollers turned country - building a following among the college age kids in the Northeast. A club opened in Harvard Square called Jonathon Swifts that became our unofficial clubhouse. We started to attract lines around the block. There was a small but wonderful country music pub in Manhattan called O’Lunney’s, the only country joint in the city, that started bringing us down for weekend engagements. We were thrilled. We were playing NEW YORK CITY! A group of us made a pilgrimage to Nashville during DJ convention and I felt like I was in the Holy Land. That really gave me the bug. I decided I was going to move to Nashville and go for it.

 

So I announced that to the band and we had about 6 weeks of gigs on the books that we would finish out. We had begun doing some recording a friend’s basement 4 track studio and two fellas approached me and said that if I came back with an album’s worth of material from those sessions, they would pay to put it out on vinyl. One of the men, Barry Glovsky, was a serious music lover and had a record review magazine, so he was “in the business”. I of course said yes, we did a few more studio cuts and got some live recordings of a few of our raucous final gigs. We pulled it all together, titled the album “Last Straw” (figuring that it was not only our first but also our last record) and I took off for a cross-country-clear-your-head trip and began to think about what to do next.

 

Then a funny thing happened. Our man Barry Glovsky started sending the record to local radio stations and music critics around the country. We started to get a very positive response. A particularly important review came from Robert Christgau of the Village Voice in New York. Christgau was, and still is, considered one of the deans of contemporary music criticism. Among other nice things, he wrote:

 

 “As befits a Yale dropout, McDermott makes country music with an air of educated subtlety – his comic sendups much more political than Jerry Reed’s and his forlorn laments a whole lot more existentialist than George Jones’s. Yet George Jones and Jerry Reed are definitively the comparison.” 

 

I believe to this day that his endorsement of that record gave other critics an implicit permission to speak well of it.  I spoke with Barry once I hit California and he offered that if I came back and did another record, he’d pull together the financing to go to a proper studio and do it right. I decided it was worth one more bite at the apple with the Chuck McDermott and Wheatstraw vehicle so I put Nashville on hold and worked my way back to Boston.

 

Upon returning, I had the opportunity to reconstitute Wheatstraw with some very talented players. Charlie Irwin on bass carried over from the prior incarnation. I invited in a very versatile piano player who had helped out on the first album named Jim Mentel who became a big part of the sound of the new band. I was able to snag the most accomplished country lead guitar player in the Northeast, former Nashville session man Rocky Stone. We auditioned a long list of drummers until we sat down with a 22 year old dynamo named Kathy Burkly who blew the rest of the field to shreds. We now had a band that could do some serious damage so we simultaneously took it on the road and into the studio.

 

We began a period of some fabulous gigs – plenty of tough ones too but many really wonderful ones. We got a lot of opening act work for national acts coming through New England – Asleep At the Wheel, Freddie Fender, Ricky Scaggs – and we played bigger and better venues. O’Lunney’s in New York gave way to The Lone Star Café, the now legendary country bar in Manhattan that developed a folklore of its own. We were regulars at the Lone Star and there was never a dull moment. Willie Nelson sat in with us one night, Johnny Cash and June Carter came in to see us another night. Oh look, there’s Andy Warhol. Belushi and Akroyd sat in a few times. Our geography expanded too. We now toured from Toronto to New Orleans. We’d hear our tunes on the radio when we played in Atlanta. We did TV shows.

 

And we put out a second record, called “Follow the Music”. It did well, especially with the critics. Rolling Stone gave it a strong boost, saying “it’s the emotion-soaked reediness of his voice that makes the aesthetic payoff”, and comparing me to my hero Gram Parsons. It raised our national profile and further upgraded our touring possibilities. But there was one thing it could not do: it could not get us signed in Nashville. We were like a quadruple contradiction in terms – “a Yale dropout long-haired country singer from Boston”. What? We got close, but we never got signed.

 

So I again concluded that I had to try something else. This time I was thinking Nashville, New York or LA. Nashville was the home of country music but it required penetrating a pretty tight-knit group down there. New York offered a foothold with the Lone Star DNA but it seemed a tough city to be penniless in. LA offered better weather (!) and a more nascent scene with artists like Dwight Yoakum and a few others breaking out of there. I put out some feelers in all three places and got a pretty solid bite in one – Los Angeles.

 

Through a friend of a friend, I was introduced to a fellow named Larry Baunach who was a seasoned record man with many years in Nashville who was managing the launch of a new record label in LA. We hit it off and Larry offered me what I thought was the most unbelievably perfect situation I could imagine. He would sign me as an artist – and he promptly flew me down to Nashville to cut three sides at Porter Wagoner’s studio with an A Team of Nashville session players AND he was going to hire me at the label to help with production and business development duties. The case was closed, I was moving to LA.