With his bobby-socks years behind him, Frank Sinatra ambitiously launched his own label. With Reprise Records, the onetime teen idol pushed into a sophisticated mid-career phase, flirting with soul jazz on 1966's That's Life and collaborating with Count Basie's orchestra on It Might As Well Be Swing, among others. Softly, As I Leave You showcases his devastating way with a string-heavy ballad.