Sinatra Rocks! Ol’ Blue Eyes' Best, Worst and Surreal Pop Covers

Legendary crooner took on songs by Paul Simon, Neil Diamond and Jim Croce

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"Both Sides Now" (1968)

Listening to Sinatra's take on Joni Mitchell's ruminations on "love's illusions" (and life's, too), you have to wonder how much he rolled his eyes when he came to the "ice cream castles in the air" line. But this lyrical, restrained rendition — clearly inspired by Judy Collins' arrangement, since it dispenses with strutting horns and has only a dab of orchestration — turns out to be a surprisingly ideal vehicle for Sinatra. Given all his years on the road, his weathered phrasing makes it clear how much he related to other lines in the song, like "Now it's just another show/You leave 'em laughing when you go."

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