Frank Sinatra's Come Dance With Me won Album of the Year in 1959. Billy May won the Grammy for Best Arrangement.
Diva: Sinatra
Mensch: May
I don't think enough credit goes to arrangers and bandleaders. Sinatra would not have been Sinatra without Tommy Dorsey, Nelson Riddle, and Billy May. They create the setting that brings out the most sparkle in his jewel.
Listen to "Day In, Day Out":
Sinatra is full of swagger, love it. But it's the Billy May arrangement that knocks me out. Those saxophones are chocolatey and the trumpets are TIGHT. Best of all, the arrangement gets out of the way for Frank - - the band fills in the blanks without drawing too much focus. I love the "all hands on deck" finish, especially the "Is he having a seizure?" drum solo.
Can there be any doubt?