Jamie Cullum

With movie star looks and vocal stylings straight out of the cool-school era of jazz troubadours, Jamie Cullum neatly bridges the gap between swingers and slackers. Fact is, the title track to his sophomore album, Twentysomething, manages to do it all in one song, as he bemoans the economic irrelevance of his liberal arts education while bopping the beat like Sinatra after a shot of Crown Royal. On his cover of "High and Dry," Cullum substitutes a supple piano backing for Radiohead's triple-guitar attack, effectively plucking the tune out of the arena and dropping it into a club. And the self-penned "Photograph," recorded for the exclusive iTunes release Live At Ronnie Scott's, showcases his gift for creating, as well as interpreting, a ballad woven from equal parts nostalgia and confession. In Next Steps, we're going to hear Jamie bring surf music into the conservatory, fuse doo-wop with hip-hop, and more.

Despite his familiarity with the pop standards that made Sinatra and Bennett household names, Jamie Cullum didn't turn off the jukebox at 1958. From the first few chords on his Fender Rhodes in "Mind Trick," Cullum tosses a musical bouquet towards Stevie Wonder's Songs In the Key of Life-era sound, complete with double-tracked harmony vocals on the chorus. On his cover of the Beach Boys' "God Only Knows," he and bassist Geoff Gascoyne tear a page out of the Elvis Costello/Brodsky Quartet songbook, with a string section lending a delicate, drawing-room intimacy to the track. And when he wraps his magic around "I Only Have Eyes for You," Cullum transports us to a smoky Upper East Side jazz bar where fedora-sporting crooners of days gone by are still revered, but hip-hop beats have snuck in the side door with the roadies.

At a time when the Great American Songbook has been pillaged by aging pop stars unwilling to hang up their rock 'n' roll shoes, British vocalist Jamie Cullum breezed onto the scene like a tenor-throated zephyr. Part Dave Frishberg, part Harry Connick, Jr., and part Orlando Bloom, the twentysomething Cullum slides comfortably between the poppier side of the jazz and rock worlds, a hipster in slacker's clothing. His influences run the gamut from too-hip-for-the-room to geek chic, always a good sign for a young artist's potential longevity; like Norah Jones, with whom he's been compared, Cullum eludes the flavor-of-the-month club in favor of the long haul. And if he's this good now, we can't wait until the moisture behind his ears dries out — when he hits his thirties and forties, the age when many jazz and pop interpreters do their best work.