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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"Something" (1980)

Making like ELP and the Clash, Sinatra went the triple-LP route with 1980's Trilogy: Past, Present, Future. For the "Present" disc, he sprinkled in then-modern pop: Billy Joel's "Just the Way You Are," Neil Diamond's "Song Sung Blue," Jimmy Webb's "MacArthur Park" and this George Harrison standard from the Beatles' Abbey Road. By then, according to session guitarist Jay Berliner, Sinatra was more at home with non-standards. "He seemed pretty sure of himself on those sessions," says Berliner. "He was most comfortable singing the swing stuff, with Don Costa and Nelson Riddle arrangements. That was his type of music. But he could handle this. I guess he wanted a new audience." Naturally, Sinatra adds his own lyrical twist ("You hang around, Jack, it might show!") but the grand, sweeping arrangement, equal parts swing band and symphony, doesn't even try to be "rock" — and is all the better for it.

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