Strolling into an East Village coffee shop, JC Hopkins looks just a little out of place. And not just because the Fort Greene, Brooklyn resident is beyond his home borough. Tall and coolly confident, immaculate in a three-piece suit topped by a tweed applejack cap, JC stands out in the neighborhood crowd of part-time punks, baggy-pants NYU undergrads, and graying bohemians.

But JC is used to it. He's always been a man slightly out of his time, looking to the past for inspiration while moving restlessly into his own future. He's been a folk-rocker, an indie-rocker, and a piano bar entertainer - all en route to his current incarnation as a composer of wry, inventive tunes and front man for one of the hippest little big bands in the country, the JC Hopkins Biggish Band.

Following in the footsteps of Hoagy Carmichael and Irving Berlin, Hopkins writes deceptively simple words and melodies that speak to something deeper, and more emotionally complex, with the potential to add a page to the great American Songbook. "It's the best of American Song from every era which most interests me," says Hopkins.

Those songs evolved into a musical theater work entitled Show Biz'ness, created by JC and poet Peter Simonelli, which ran for six months in San Francisco. The show gave rise to two important songs: "Show Biz'ness," newly recorded for Underneath A Brooklyn Moon; and "Dreams Come True," covered by Willie Nelson and Norah Jones on Willie's album It Always Will Be (2004, Lost Highway).

In 2000, JC moved to New York. He started gigging around town at clubs like Fez, Tonic, and The Slipper Room with a core group of players that included Norah Jones on vocals. (JC and bassist Lee Alexander co-wrote "Painter Song" for her 2002 multi-platinum debut Come Away With Me.) He also found session work with some of the greats, tracking with Band alumni Levon Helm and Garth Hudson, producing and playing piano on Victoria Williams' 2000 album 'Water to Drink.'

JC's Biggish Band continued to germinate, attracting a variety of top New York players, and drawing sell-out crowds on both coasts at tastemaker venues such as NYC's Joe's Pub, and LA's Largo. Singers as diverse as Victoria Williams, Martha Wainwright, Syd Straw, and Madeleine Peyroux (who co-wrote four songs included on Underneath A Brooklyn Moon), fronted the band, before Queen Esther became the primary vocalist. "Queen Esther's voice has the strength and style of Betty Carter or Sarah Vaughan, real favorites of mine," says JC. In 2006, JC was invited to produce an album of children's music with writer/actor John Lithgow. "The Sunny Side of the Street," was nominated for a Grammy award in 2007. A live show, "John Lithgow: The Sunny Side of the Street," performed on Broadway at the New Victory Theater in New York in Early 2008, for which JC was musical director. As a playwright, JC has written a two-act romantic tragedy, "Rose does Rico," a three-act post- 9/11 drama, "The Conspiracy Theorist," and is currently at work on a burlesque-swing musical, "Underneath a Brooklyn Moon." "It's just been one thing leading naturally to another," Hopkins muses, "but don't ask me what comes next!"