20 Times Artists Dared to Sing Sinatra’s Signature Hits

Coleman and Carolyn Leigh wrote this in 1959, and Sinatra’s 1964 Basie recording became one of his most swinging and optimistic performances, chosen later as the inscription on his gravestone. Wilson’s jazz phrasing gave the lyric a maturity and specificity that matched her own vocal intelligence rather than replicating Sinatra’s outward confidence. Her version is the most technically accomplished jazz cover on this list, built from the inside of the tradition rather than admiring it from a respectful distance.