I Left My Heart In San Francisco
by Tony Bennett
Released: Jan 1962
This one doesn't play like a cohesive concept album but it remains an essential part of American culture. The title tune was a surprise monster hit and it remains the number that Bennett is most associated with. The other essential songs here are "The Best Is Yet to Come" (which Cy Coleman wrote for Sinatra but Frank waited to record it with Count Basie) and "Smile," the Charlie Chaplin-penned heart-breaker.