Bebop Bailey

One of the classic stereotypes of our community is that lesbians dig chicks with guitars. But the truth is, it all depends on what kind of music is coming out of that Stratocaster. Just ask Sheryl Bailey, who despite being one of the leading jazz guitarists of her generation, and out to boot, hasn't exactly been embraced by the queer community.

"My audience tends to be young white males," laughs Bailey, who's not expecting to see a lot of sisters in the house when she plays The Regattabar next week with her trio, The Sheryl Bailey 3. "The lesbian community just isn't that connected to jazz."

"It used to frustrate me," she admits. "I'd put together jazz nights for lesbian clubs, and the audience couldn't wait for us to finish so they could put on the Melissa Etheridge."

Bailey is receiving plenty of attention from other quarters. She's been praised many times by Guitar Player magazine, (which notes that she ""has one of the warmest and most compelling tones of her generation,") profiled in The Advocate, and a reviewer for soundstage.com recently raved "I can't think of a young guitarist who has impressed me more in the last few years." No wonder the Pittsburgh native and Berklee grad gigs regularly at the top New York City jazz clubs, where she's made her home for the last 15 years.

Growing up in an artistic family from Pittsburgh, Bailey had an early exposure to music. "Everyone in my family is musical," she says, including her mother and grandmother, who were professional musicians. "I thought it was normal that your mother could sit down and play 'Rhapsody in Blue," Bailey recalls. "I thought everybody sat down and sang show tunes."

Not fully appreciating her luck, Bailey devoted herself to rock and roll in her teen years. "I had to play classical piano when I was a kid," she explains, "and just to be a rebel I started the guitar. I had basement bands. I was playing bars when I was 15, doing classic rock and hard rock.

"I was already serious about the guitar," she continues, "and then I stumbled across a jazz radio station playing some Wes Montgomery. Jazz just drew me in and I fell in love with it." Montgomery would become one of her biggest influences, along with Pat Martino and Grant Green.

Incidentally, Bailey recommends bebop in general, and Montgomery in particular, as being very accessible to people wanting to learn more about jazz. "All his music feels good," she says enthusiastically. "I love the harmony and the energy of bebop. It's so uniquely American, especially with the African-American struggles of that time channeled into it."

Bailey took that energy to Boston's Berklee College of Music, where she found time to help get the school's first LGBT student group off the ground. "I still find Berklee to be a little homophobic," she says, reminding me of the controversy when Berklee's then-president, Gary Burton, came out in the 90s.

"I think the men have a harder time," she muses, "because there is a bit of machismo in playing jazz. People are willing to accept some dykes. I haven't ever had anyone really get in my face or make me uncomfortable."

After graduation, Bailey landed a job teaching in Baltimore, but soon New York City beckoned. It wasn't easy leaving behind a steady salary, but Bailey "needed to get [her] ass kicked." She says in some ways her musical education didn't really begin until she entered New York's jazz scene. There she had to compete with the best of the best, and she began learning the tiny details - like holding her guitar pick at just the right angle to produce the warmest tone, or which guitar strings produce precisely the right sound - that separate the good from the great.

While establishing herself as a premier jazz guitarist and releasing five CDs, Bailey also found time to return to Berklee to teach. These days she returns to Boston once or twice a week to coach young guitar players. Surprisingly, her upcoming show at The Regatta is her first local appearance outside of Berklee.

"I'm so excited for this show," she says. "This band has been together since 2001, so we're a tight unit. And we're going to be trying out some new material that we'll be recording for a DVD in May." The prolific Bailey is also featured on a tribute to jazz guitarist Emily Remler, due out in August from Telarc Records.

Although Bailey prefers self-producing, she was happy to make an exception for the Remler project. "The producer of that one has won four Grammys, so I think I'm good in good hands," she chuckles.

The Sheryl Bailey 3 plays Tuesday, April 29 at 7:30 p.m. at The Regatta Bar, 1 Bennet St., Cambridge. Tickets $15, available at www.regattabarjazz.com or 617.661.5000.