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

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

Frank Sinatra

Late in his career, Frank Sinatra gave his own spin to a handful of rock hits.

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On two different levels, Bob Dylan's new Shadows in the Night, out this week, got us thinking about Frank Sinatra. First is the obvious reason: Although technically not a Sinatra "tribute," Dylan's record features his takes on songs Sinatra covered at various points in his life. Which, in turn, reminded us of the bizarre-world opposite scenario: the numerous times in his career that Sinatra waded into rock & roll.

In the Fifties, Sinatra made his contempt for rock more than obvious. In an article he wrote for a French magazine in 1957 — then widely reprinted in the U.S. — he decried what he called "the most brutal, ugly, degenerate, vicious form of expression it has been my displeasure to hear, and naturally I'm referring to the bulk of rock 'n' roll…. It fosters almost totally negative and destructive reactions in young people. It smells phony and false. It is sung, played and written for the most part by cretinous goons and by means of its almost imbecilic reiterations and sly, lewd — in plain fact, dirty — lyrics, and as I said before, it manages to be the martial music of every sideburned delinquent on the face of the earth." (Sinatra himself didn't exactly associate himself with the most wholesome characters on the planet, but that's another story.)

Roughly a decade later, with rock now commandeering the charts and crooners in danger of extinction, Sinatra softened a bit. From then through the early Eighties, he took periodic stabs at post-Elvis pop and rock songs: Paul Simon, Jim Croce, Neil Diamond, Jimmy Webb and Billy Joel all got the Ol' Blue Eyes treatment. Here are the surprising highlights — and surreal low points — of the times Sinatra tried to rock out.

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THE TONIGHT SHOW STARRING JOHNNY CARSON -- Air Date 09/17/1965 -- Pictured: Singer/actor Frank Sinatra on September 17, 1965 (Photo by Fred Hermansky/NBC/NBCU Photo Bank via Getty Images)

“Sweet Caroline” (1974)

A surprisingly joyless version of the Neil Diamond anthem. (Years after Sinatra's death, Diamond admitted he was inspired to write the song after seeing a photo of Caroline Kennedy; knowing Sinatra was an early supporter of JFK, one wonders what he would have made of that tidbit.) Sinatra manages to rouse himself during the "hands, touching hands/reaching out, touching me, touching you" part, but otherwise he sounds strangely removed, as if he couldn't wait to finish the take and go back to hanging out with Jilly Rizzo. Sinatra's later cover of Diamond's "Song Sung Blue" is a slight improvement.

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THE TONIGHT SHOW STARRING JOHNNY CARSON -- Air Date 09/17/1965 -- Pictured: Singer/actor Frank Sinatra on September 17, 1965 (Photo by Fred Hermansky/NBC/NBCU Photo Bank via Getty Images)

Frank Sinatra

“Bad, Bad Leroy Brown” (1974)

It's easy to see how Sinatra would connect to Jim Croce's thumping, barrelhouse hit inspired by an AWOL escapade of an ex-Army buddy. The song adapts surprisingly well to its big-band overhaul, and it wouldn't be a Sinatra cover without a few lyrical tweaks: "A man named Leroy Brown" becomes a "cat…," and "All the men just call him 'sir'" becomes "All the studs…" Still, it's preferable to last year's deplorable "Leroy Brown" parody, which was written by a California ex-cop who used it as a way to mock the shooting death of Michael Brown.

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THE TONIGHT SHOW STARRING JOHNNY CARSON -- Air Date 09/17/1965 -- Pictured: Singer/actor Frank Sinatra on September 17, 1965 (Photo by Fred Hermansky/NBC/NBCU Photo Bank via Getty Images)

“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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THE TONIGHT SHOW STARRING JOHNNY CARSON -- Air Date 09/17/1965 -- Pictured: Singer/actor Frank Sinatra on September 17, 1965 (Photo by Fred Hermansky/NBC/NBCU Photo Bank via Getty Images)

“Bang Bang (My Baby Shot Me Down)” (1981)

First sung by his then-wife Cher in 1966, Sonny Bono's tale of a clearly dysfunctional relationship made like a folk-rock novelty song. (On the plus side, it set Cher on the story-song course that led to more enduring triumphs like "Gypsies, Tramps and Thieves" and "Half-Breed.") Slowed down and turned into a piece of theater, Sinatra's version is dark and melancholic — as much a dramatic reading as a mere remake. Sinatra's last stab at rock (his next — and final — solo studio album, L.A. Is My Lady, returned him to the land of Cole Porter and Harold Arlen) but a nice way to go out.  

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