This is the story of Bob Woodruff, a guy who went to Nashville, made two fantastic, out-of-step records at mainstream country’s ground zero, and then simply disappeared. It’s a story of a string of bad luck that led to Woodruff becoming a subject of those “whatever happened to” queries, and then, 20 years later, a swing from bad luck to good, and a return.

Woodruff moved to Nashville from his native New York City after signing a record deal with Asylum Records, and released “Dreams & Saturday Nights” in 1994. The country music found therein — muscular, tough honky-tonk, shot through with rock and soul — was out of step with pretty much everything else that was happening in the genre, including the hat-act progeny of the neo-traditionalists who’d shown up toward the end of the previous decade.


“I was up against a Nashville that I wasn’t really aware of,” observes Woodruff, reached by phone at his Los Angeles home. “After having moved there, I eventually learned that the sweaty human realism that the singers who inspired me were most about wasn’t really in vogue there at the time. My idea of country music came from things that were rooted more in my imagination.”

Asylum had just been resurrected as a country imprint, and Woodruff thinks the label’s view was that there would be room for records like his within the mainstream. “It wasn’t really an effort to find a place outside of mainstream country, because there wasn’t another genre,” he says. “The genre called ‘Americana’ wasn’t really in place.”

His record was a critical success, but turned out to be a commercial disappointment that wasn’t properly supported. He believes the label did the best it could: “That time at country radio, it was a tough fit. As much as Asylum wanted to try to do something different, they were still operating like most labels in Nashville at that time, relying mainly on country radio to break records and artists.”


After Woodruff and the label parted ways, he made an equally compelling follow-up for another new venture, Imprint Records — which promptly went out of business. “That was a heartbreaker, I’m not going to lie: We had a lot of high hopes for that record,” Woodruff recalls.

Add yet another attempt with another label that didn’t even see release, and the cumulative effect threw Woodruff for a serious loop. He moved back to New York to be near his seriously ill mother and, as the singer wryly puts it, “began to pursue other interests” — one of which was heroin. “That really took me out of the game for quite a few years. I was at a place where I was feeling so hopeless and despairing of ever making another record, and fell into a depression. And that was kind of my way of coping with it for a time.”

Woodruff finally ended up in Los Angeles, where he kicked his habit. While he’d never stopped making music for himself, not much more had happened for a while: “I was just concentrating on living my life and enjoying life as a guy who was clean and sober.” But he says that he had always had it in the back of his mind to make “a so-called comeback record.” He had an idea of how he wanted to do it; he was trying to be patient, and get his ducks in a row. And then, out of the blue, it just happened.


Having toured Sweden with the band Shurman in 2012, he stayed on afterward to decompress and enjoy the country. One of the tour promoters asked if he wanted to do a few more shows with some local players. “These guys were really fine musicians, really cool guys, and they had this great studio,” Woodruff says. “So instead of just rehearsing, we began hitting the ‘record’ button. And then we thought, well, let’s just go ahead and do a whole record while I’m here. So in just a few days we did the bulk of the album.”

The spontaneity was completely different from how Woodruff had approached recording before. What resulted was the core of his new release, “The Year We Tried to Kill the Pain,” a slightly (but only slightly) less twangy compendium of vintage Woodruff distillations of romantic pain and desperation that reveals he hasn’t lost a step in the two decades since his previous record.

“You’ve waited 20 years to make another record, and then it happens: You get the opportunity to do it in another country with people you don’t know,” he says with evident appreciation of the irony. “And I’ve got more songs. I can’t wait to make another record. I wonder what country that’s going to be in.”

Bob Woodruff


At Thunder Road, Somerville, March 24 at 7 p.m. Tickets: $8. 866-468-7619, www.ticketweb.com

Stuart Munro can be reached at sj.munro@verizon.net.