"Mrs. Robinson" (1969)
Few moments embody the generation gap of the Sexties more than Sinatra's gin-and-tonic takeover of Simon & Garfunkel's hit from the soundtrack of The Graduate. The brassy-fanfare arrangement that tries to imitate Paul Simon's guitar lick is clunky enough. The uncredited rewrites of the lyrics are downright cringe-worthy: the way Sinatra inserts the name of his restaurateur pal Jilly Rizzo ("Jilly loves you more than you will know!") or the insertion of an all-new verse. "And you'll get yours, Mrs. Robinson — foolin' with that young stuff like you do... Boo hoo hoo!" — he cut the line about Joe DiMaggio for that?