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Harry Connick Jr. has spent his entire career doing much more than what people expect of him – except once. When the 22-year-old jazz-pop wunderkind (he made his first record at age ten) from the Big Easy was tapped to perform songs for the soundtrack of When Harry Met Sally, he delivered pretty much exactly what the film required: a fresh and competent take on romantic standards, the perfect counterpoint to a story about an all-too modern love affair. People wanted to know: who was the man behind the smooth, Sinatra-esque vocals? When they saw him, they – at least, the women and the gay men – wanted to see a lot more of him. Connick, a born overachiever, was happy to oblige, in his half suave, half southern-fried way.

Over the past 20 years, Connick has recorded 21 albums; in addition, he’s appeared in over 20 films, co-starred on Will & Grace for four seasons, and worked on Broadway as both a performer and a composer. He pops up everywhere, from TV specials to PSAs on the importance of obeying gun laws. The record that guaranteed he would not become a just a footnote in show business history, coming hard on the heels of his success (and Grammy award) for Harry/Sally, was We Are in Love, which showcased Connick as a songwriter and bandleader as well as singer and pianist. Those who think Michael Bublé originated the role of  “post-rock pop-standard hottie” have obviously forgotten the tizzy Harry caused with his deliciously square lyrics (check out “Recipe for Love” or “Heavenly” for examples) and his old-fashioned earnestness about music and love: he publicly gushed over his underwear-model girlfriend (to whom he has been married since 1994) and declared he would never take an acting role which required him to kiss a co-star, as that would constitute cheating. Obviously, Harry reconciled his ambitions as an actor with his moral code over time, sucking face with quite a few Hollywood leading ladies, but he has remained true to his musical roots – classic vocals, jazz piano, New Orleans flavor, big band sound.