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"Didn't We" (1969)

Few modern writers wrote songs as fits-like-a-glove as Jimmy Webb, and thankfully Sinatra knew it, cutting tracks like the epic "MacArthur Park" and the almost-as-forlorn "By the Time I Get to Phoenix." Richard Harris and Glen Campbell, respectively, owned those covers, but no one inhabited "Didn't We" better than Sinatra. In a song that amounts to one long whiskey-soaked regret, you wonder if the lyrics took the singer back to his tumultuous Ava Gardner years.