But today, Masterson — who performs in Palo Alto's Brown Bag Concert Series on July 31 — isn't singing only the blues. Instead he is renowned for playing a lively mix of jazz, Brazilian and Cuban music that the JazzTimes magazine once called "a certified treasure."
"I had a very hard childhood, but at the same time today I'm a happy person and I don't have any regrets," Masterson said in an interview.
After his emancipation from the foster-care system, Masterson went to college and eventually studied music in Latin America, including two years in Brazil and nine consecutive trips to Cuba.
This time in Latin America profoundly influenced his first two CDs, "Intercambio" and "Cubacambio." According to Masterson, however, this earlier music was less personal than his more recent work.
"I was trying to become a commercial success; I wanted to be played on the radio stations and that didn't happen the way I wanted it to," he said. "I became disillusioned, but I also promised myself that I would never do that again — I wasn't going to make commercial concessions."
So Masterson began to self-produce his CDs, drawing on personal experiences to influence his work.
"All of my songs became personal expressions of things that I had gone through, things that I was going through," he said. They include a piece called "Student Loan," which Masterson wrote right after he got out of college and was facing a huge debt.
"I'd say that the experiences I had when I was young gave me a lot of tools to deal with diversity and to be more open-minded," he said. "I just feel an affinity with everybody — wherever I go, whatever culture, whether it's San Francisco or the other side of the world, I feel like I can relate to everybody."
So it is little wonder that Masterson's music appeals to a broad range of musical tastes. His upcoming concert in Palo Alto will continue to broaden that range, with his first public performance of classical music with the Damien Masterson Ensemble.
Masterson's foray into classical harmonica had a serendipitous start.
"It's an interesting story," he said. "About three or four years ago I was practicing in the living room with the door open and someone walked in. As it turned out, I have a neighbor who is a renowned classical guitarist who also plays Brazilian music and other styles."
That neighbor was Rick Heizman, who now plays classical guitar for the Damien Masterson Ensemble. The two started working out some classical pieces together. Later, the ensemble expanded to include Robert Schwartz on the piano.
Now, Masterson's repertoire features music from Bach, Mozart, Debussy, Brahms, Beethoven and Ravel. "I call it light classical because I'm not classically trained," he said. "There are quite a few figures out there who are brilliant classical harmonica players, and God only knows how they got their training."
Classical music on the harmonica isn't as impossible as it might sound. In fact, the chromatic harmonica that Masterson plays can reach all the same notes as a piano.
Masterson also plays the saxophone, but said he "wouldn't dare present myself paying classical music on sax because there's such a strong classical history there." He added, "But in this case, because it's the harmonica, I feel like we have a little more leeway — or at least I'm hoping."
The Palo Alto performance will also include some of Masterson's trademark Latin and jazz-inspired harmonica. Whatever the genre, when Masterson is playing that instrument, something just seems to click.
"I always get positive reactions on the harmonica," he said. "If the universe has been trying to tell me anything, it's 'stick with the harmonica, kid.'"
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