Harry Connick, Jr.

At the end of the ’80s, the Billboard charts weren’t exactly crowded with Sinatra-style crooners — but that’s part of what made Harry Connick, Jr.’s arrival such a breath of fresh air. Though Connick was a child prodigy who kicked off his recording career at age ten, it was his suave-but-swinging approach to standards like “It Had to Be You” and “Don’t Get Around Much Anymore” on the When Harry Met Sally soundtrack that really earned him a place in America’s heart. And when he laid his luscious pipes across everything from the traditional Irish air “Danny Boy” to the Lee Dorsey R&B grinder “Working In the Coal Mine,” it was obvious that he was no one-note Johnny.

In Next Steps, find out why Harry holds his hometown close to his heart.

New Orleans native Harry Connick, Jr. may have made his name with big-band swing, but his Crescent City roots always shone through too. He offers up a simmering, soul-soaked take on Allen Toussaint’s funky anthem of positivity “Yes We Can Can,” and comes off like a Dr. John disciple on the self-penned, second-line-slammin’ Mardi Gras party tune “Here Comes The Big Parade.” Even Connick’s piano overflows with New Orleans pride, as he reaches back to the beginnings of jazz and hammers out the stompin’ ragtime riffs of Kid Ory’s “Muskrat Ramble.”

Piano prince Connick is a killer on the keys, in Deep Cuts.

Harry Connick, Jr.’s cool, caressing croon crossed him over from jazz journeyman to pop star, but his piano wizardry earns plenty of acclaim on its own. He blows bebop kisses to Tchaikovsky’s dreamy, tinsel-toed “Dance of the Sugarplum Fairies,” and lets the Big Easy blues drive his digits across the ivories on “Bayou Maharajah.” And when Connick lets his Monkish moves and salty, sideways harmonies dance a twisting, twirling tango across the steady-swingin’ shuffle of “Oh! Ain’t That Sweet,” he proves he could’ve carved out a princely career without ever singing a lick.

Imagine pinup-idol-era Frank Sinatra with Dr. John’s New Orleans-schooled piano prowess; add a touch of funk, a dash of Monk, and the killer charisma of an Entertainer with a capital E, and an artist who looks a lot like Harry Connick, Jr. starts to come into view. Whether he’s laying down the second-line street-parade rhythms that are in his blood; crooning a cool, jazzy ballad; belting out a big-band swinger; or pounding out some powerful piano licks with his blues-bent bebop chops, Connick carries himself with sure-footed style. Maybe that’s what helped make him one of the biggest-selling jazz artists ever, who’s able to translate his talent to stage, screen, and record with equal ease. We’ve combed through every inch of Connick’s career — even peeking in the cracks between the piano keys — to give you 75 solid reasons to be wild about Harry.