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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)

“Winchester Cathedral” (1966)

Earlier in '66, Sinatra recorded a cover of Petula Clark's "Downtown," but this remake of the New Vaudeville Band novelty hit marked the beginning of his deeper dive into then-current pop. The original, an ersatz Brit-music-hall fluke complete with a fake-megaphone voice, wasn't much to begin with, and Sinatra seems a bit lost in this brassy-cheesy arrangement, even when he ad-libs, "Man, you brought me down!" He clearly relishes sinking his teeth into the line "My baby left town!" — but still not a promising start to the Sinatra "rock" years.

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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)

“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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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)

“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?

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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)

“For Once in My Life” (1969)

From the same My Way album that gave us that questionable "Mrs. Robinson" is this far more satisfying take on Stevie Wonder's jubilant hit. The frisky Motown guitar lick of Wonder's version is gone, but Sinatra's sure-footed phrasing, combined with longtime collaborator Don Costa's arrangement, deepens the romantic elation of Wonder's original. You almost wish Sinatra had tackled "Sir Duke" at some point.

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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)

“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.

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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)

“Leaving on a Jet Plane” (1971)

John Denver's melancholic ballad about hitting the road and leaving behind his loved one (a hit for Peter, Paul & Mary) sounds like it was written for Sinatra, even if it wasn't. The sense of road weariness heard in "Both Sides Now" is even more ingrained here: You can hear in Sinatra's voice all the years of touring, sleeping in hotels and hanging out in dressing rooms. Except for a splash of brass in the chorus, the arrangement mostly restraints itself. One of the highlights of Sinatra's pop period.

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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)

“Nobody Wins” (1973)

By the early Seventies, Sinatra's increasingly leathery voice found a perfect companion in this end-of-an-affair rumination by another rough-sounding singer, Kris Kristofferson. The strings are a bit overdone at times, but at least Sinatra dispenses with the countrypolitan backing vocals of Kristofferson's version. A rare case of Sinatra besting the original.

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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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