He does remind me a lot of Harry Connick, Jr--my wife REALLY LOVES Connick.
Great vocal skills in both--trying to break in as something VERY like older "crooners", and Ole' Blue Eyes Himself, is a TOUGH gig! I didn't much like some of original "Rat Pack's" stuff, or Sinatra's Mafia connections (he was supposedly the original model for the singer character in the original "Godfather", for whom a horse was decapitated!).
I LOVE all sorts of jazz; though.
I still love a lot of old rock n Roll, too.