With a career that spanned nearly half a century, and enough love songs to overwhelm even the most stoic bride, Frank Sinatra’s Rat Pack–era coolness and fantastic charm became the stuff of legend. Throughout his career, he cut a path through “Bobby Soxers” and screen sirens alike, who were but moths drawn to his flame. Ava Gardner and Mia Farrow were no match for his chiseled face and those piercing blue eyes, and there’s no question he has us transfixed as well. Combined with his debonair style and iconic voice, it’s hard to imagine a guy with that kind of class around today. We’d do just about anything to sit across from him at a dimly lit red-sauce-only Italian joint.