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His distinct tunes eventually did start winning people over. Go-go godfather Chuck Brown gave him encouragement. WHFS’s Bob Waugh began playing his music on-air. Fans poured out to hear Mr. Greenwood sing and strum his oddly tuned guitar (which has no bottom E string and its B tuned to B-flat).

But even after he moved to Brooklyn and landed his first recording contract, things didn’t always go smoothly for the artist. His first label shelved the concept album he made, and Mr. Greenwood says that the three labels he’s been on since haven’t exactly rushed to get his tunes on the radio. Moreover, he’s not currently signed and doesn’t plan on inking another traditional contract.

“So I go on the road; that’s been the story of it,” he says, sounding not bitter but pragmatic.

In truth, he’s had a little help spreading the word about his music lately, and we’re not just referring to the word-of-mouth that’s been so valuable to him. We’re talking about licensing deals — with Pontiac, NBC’s “Scrubs” and the film “Alpha Dog” (released earlier this year) to name a few. It’s just another way of “getting the music to the people,” Mr. Greenwood says.

Ever the poet, he manages to find a silver lining in what he describes as a struggle to be heard and build an audience. “What’s beautiful,” he says, “is that this is still underground music. It’s still on the rise.”

Citizen Cope plays Thursday at the 9:30 Club (www.930.com), Dec. 28 at Baltimore’s Rams Head Live! (www.ramsheadtavern.com), and Feb. 6 at Towson’s Recher Theatre (www.rechertheatre.com). The first two shows are sold-out.