"Winchester Cathedral" (1966)
Earlier in '66, Sinatra recorded a cover of Petula Clark's "Downtown," but this remake of the New Vaudeville Band novelty hit marked the beginning of his deeper dive into then-current pop. The original, an ersatz Brit-music-hall fluke complete with a fake-megaphone voice, wasn't much to begin with, and Sinatra seems a bit lost in this brassy-cheesy arrangement, even when he ad-libs, "Man, you brought me down!" He clearly relishes sinking his teeth into the line "My baby left town!" — but still not a promising start to the Sinatra "rock" years.