Adamzinke · CC BY-SA 4.0

Harry Connick Jr. built a career that straddled two worlds: as a jazz pianist and singer out of New Orleans, he racked up more number-one albums on the U.S. jazz chart than any other artist in its history, alongside three Grammy Awards. He crossed into film with a supporting role in Memphis Belle and later played opposite Sandra Bullock in Hope Floats, and spent four seasons as Grace's husband Leo on Will & Grace, earning two Emmys along the way.