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Legend’s embrace of the genre was alternately cool and clumsy

Frank Sinatra_My Way cover cropFrank Sinatra covered a lot of ground as an entertainer, and this year’s celebration of his centennial birthday (Dec. 12) would not be complete without revisiting his complicated relationship with rock ’n’ roll (and also the pop music that shared rock characteristics).

Sinatra’s awkward association basically started in October 1957, when the Associated Press picked up on an article he wrote about American music that ran in Western World, a Paris publication. On the subject of rock ’n’ roll, Sinatra wrote that it “smells phony and false,” was “sung, played and written for the most part by cretinous goons” and contained “sly, lewd — in plain fact dirty — lyrics.”

Harsh words, for sure, but they fit the persona and echoed the standards of the often-tuxedoed, stiff-drink-in-hand man’s man known as The Chairman of the Board. As it turns out, not too long after that assessment of rock, Sinatra became part of that wide-ranging scene — and he would revisit it from time to time with mixed results throughout the rest of his career.

Performing alongside Elvis Presley

While in Los Angeles for a show at the Pan Pacific Auditorium in late October 1957, Elvis Presley was asked how he felt about Sinatra’s comments, and the acknowledged king of rock ’n’ roll took the high road with his response.

“He has a right to his opinion, but I can’t see him knocking it for no good reason,” Presley told Dolores Diamond of Dig magazine. “I wouldn’t knock Frank Sinatra. I like him very much. If I remember correctly, he was also part of a trend, just like rock ’n’ roll.”

Frank Sinatra and Elvis Presley_1960

Three years later, Sinatra was part of that trend — with Presley by his side. Weeks after his March 1960 discharge from the U.S. Army, Presley went to the Fontainebleau Hotel in Miami Beach for a taping of The Frank Sinatra Timex Show. Subtitled Welcome Home Elvis, the 60-minute TV special (which aired May 12, 1960) also included comedy bits and music featuring Sinatra’s daughter Nancy Sinatra and his cronies Sammy Davis Jr., Peter Lawford and Joey Bishop.

In Charles Pignone’s book Sinatra 100, Nancy Sinatra says her father and Presley were nervous, but smiles and laughs abound throughout their screen time alone and together. The big moment between them takes place about 45 minutes into the festivities when they perform a mashup duet of signature hits. Rock ’n’ roll it is not: The music leans more toward the kind of finger-snapping groove and brassy instrumental arrangement often found in Sinatra’s catalog. But in this moment of pop-culture and generational crossover, the core material mattered the most: With signature grace and authority, a smiling Sinatra sings lines from the 1956 Presley ballad “Love Me Tender” (while Presley does some of the 1958 Sinatra smash “Witchcraft”). Sinatra’s choice was a safe one — it’s not like he tackled “Jailhouse Rock” or anything. He had to feel some level of pressure with rock ’n’ roll’s biggest star (20 years his junior) standing right next to him, and in the end, Ol’ Blue Eyes did not embarrass himself.

A hit duet with his daughter

Sinatra surely would have looked foolish (and desperate) if he’d pushed his rock ’n’ roll involvement right after the Presley special. Instead, as the 1960s unfolded, Sinatra continued with his classy pre-rock pop standards — and in doing so, occasionally conjured up thoughts of Presley’s subtler, smoother side with songs such as “Softly, As I Leave You” and “Available,” both from 1964.

By 1967, rock ’n’ roll had changed and grown tremendously since Sinatra’s comments 10 years prior. But even so, a level of sophistication — in the form of carefully arranged string and wind instruments — could be found on rock recordings that also had prominent guitars and firm backbeats, thanks in part to the likes of The Beach Boys, The Righteous Brothers and The Mamas & the Papas. (Like Sinatra, they all recorded with the famed L.A. session group known as The Wrecking Crew.) And with “Somethin’ Stupid,” Sinatra found a place within that broadening pop-music landscape.

Nancy and Frank Sinatra_Somethin' Stupid 45

Teaming up with daughter Nancy for this duet had to be a risk because of what she presented to the eyes and to the ears. With her long hair, short dresses and go-go boots, Nancy’s swingin’-1960s sex appeal no doubt helped propel the come-hither pop of her singles “These Boots Are Made for Walkin’ ” and “Sugar Town” into the Top 5 of Billboard’s Hot 100 in 1966.

She is much more demure vocally on “Somethin’ Stupid.” As for her father, once again he finds a way to be contemporary while retaining his dignity. The Sinatras sound sweet together throughout the song. The result was the first father-daughter duet to hit No. 1 on the pop-singles chart; it knocked The Turtles’ “Happy Together” from the top spot and spent four weeks there before being ousted by The Supremes’ “The Happening.”

Venturing into another dimension

Maybe it looked really good on paper. It certainly did not look good on TV.

On Nov. 25, 1968, NBC aired the prime-time special Francis Albert Sinatra Does His Thing, and the title wasn’t the only thing that was far out, man. Sinatra’s age-inappropriate wardrobe choices eclipse the music for a good part of the 60-minute special, most egregiously during “Sweet Blindness” with special guests The 5th Dimension.

Singing that song with the saccharine vocal quintet made sense, as Sinatra was in the early stages of embracing material by rock singer-songwriter types. When Francis Albert Sinatra Does His Thing aired, his current studio album was Cycles, which featured his renditions of songs written by Joni Mitchell and Jimmy Webb. Another highly regarded songwriter, Laura Nyro, wrote “Sweet Blindness,” a Top 40 Billboard pop hit for The 5th Dimension in late October 1968.

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Sinatra’s embrace of contemporary fashion failed him on this night, though. For the performance with the overly earnest 5th Dimension, he sports white shoes, white slacks and a ruffled blue jacket — basically groovy giftwrap as clothing for a man in his 50s. Sinatra sings a few lines of “Sweet Blindness” by himself, and while he sounds just fine in those solo moments, his involvement is really just a cameo role — and not exactly a scene-stealer. (This segment really deserves its own name: The 5th Dimension Does Its Thing — And Frank Sinatra Offers a Glimpse of His.)

At the end, Sinatra says, “And don’t look now, Francis Albert, but your generation gap is showing.” Scripted or not, the line perfectly summed up what had just happened.

Jilly and Jack: Interpreting Simon & Garfunkel and The Beatles

Sinatra continued to perform and record contemporary rock and pop tunes into the early 1980s. He had a thing for redoing former No. 1 singles, such as “Yesterday,” “Leaving on a Jet Plane,” “You Are the Sunshine of My Life” and “Bad, Bad Leroy Brown,” but of these, only his cover of Jim Croce’s “Leroy Brown” charted on the Billboard Hot 100, peaking at No. 83 in 1974.

Frank Sinatra_Mrs. Robinson single sleeve copy

Sinatra’s takes on two other high-charting hits best represent this particular period of his rock-flavored resume. In doing Simon & Garfunkel’s “Mrs. Robinson,” Sinatra sings drastically different lyrics that reflect his life, both directly and vaguely.

Right off the bat, he drops the reference to Jesus and replaces it with “Jilly,” a nod to his close pal and restaurant owner Jilly Rizzo. There’s no mention of baseball great Joe DiMaggio, who was a Sinatra friend in the 1950s before they had a huge falling-out (fueled in part by rumors that Sinatra had hooked up with DiMaggio’s ex-wife Marilyn Monroe).

And then there are these entirely new lines: “And you’ll get yours, Mrs. Robinson/Fooling with that young stuff like you do/Boo hoo hoo, woo woo woo.” Fresh from ending his two-year marriage to model-actress Mia Farrow (who was 30 years his junior and actually five years younger than stepdaughter Nancy), maybe Sinatra was having a little fun at his own expense.

Frank Sinatra_Something single copy

Sinatra once described the George Harrison-penned Beatles hit “Something” as “one of the best love songs to be written in 50 or a hundred years.” That didn’t mean it was sacred text. Sinatra makes a notable alteration to the bridge — and thus makes the song his. Just by addressing the would-be listener as a generic “jack” — “You stick around, jack, it might show” — he instills signature Sinatra bravado, transforming the line into a mild dare that minimizes the uncertainty of the “I don’t know” refrain that follows.

This ‘Lady’ Is a Dud

For 1984’s L.A. Is My Lady, Sinatra stayed away from famous rock-related material (his version of the often-covered, Bobby Darin-associated “Mack the Knife” doesn’t really count). Instead, he recorded songs by the likes of Cole Porter, Sammy Cahn and Harold Arlen and worked with his old friend and onetime producer Quincy Jones (fresh from the megasuccess of Michael Jackson’s Thriller).

Those elements, combined with the Jones-led orchestra, make this an old-school Sinatra album (though not necessarily a great Sinatra album). So it’s all the more puzzling why rockers and other contemporary personalities appear throughout the video for the album’s synth-accented, mildly tropical-feeling title track.

Roth and Van Halen

The video opens with Van Halen’s David Lee Roth and Eddie Van Halen fighting their way through a post-concert crowd and entering a limousine. “A little Frank Sinatra for ya here,” Roth says as he pulls a VHS tape from his bag, then loads it into the car’s VCR.

From there, it’s a game of “Spot the Celebrity Doing Everyday Stuff”: Donna Summer as a waitress; Michael McDonald bagging groceries; Missing Persons singer Dale Bozzio being carried on a surfboard along the beach, and so on. Mixed in with the recent footage are classic clips of Sinatra from various stages of his career, including a segment from his 1960 TV special with Presley.

MTV did give the “L.A. Is My Lady” video some airplay, but as for the single, it didn’t even dent the Billboard Hot 100.

Duets from a distance

For his final two new studio albums, Sinatra remade selections from his back catalog with myriad big-name singers — including a few bona fide rockers.

In his book Making Records: The Scenes Behind the Music, producer Phil Ramone writes that Sinatra didn’t dismiss this idea out of hand but was skeptical. After some back and forth with Ramone, Sinatra agreed to do it, insisting that nobody else sing in the studio with him. That prompted Ramone to use fiber-optic lines to record the guest singers’ parts from afar (which did not sit well with music critics in their subsequent reviews of the album).

Frank Sinatra_Duets cover

On 1993’s Duets, U2 frontman Bono is featured on “I’ve Got You Under My Skin.” Recording in Ireland sans Sinatra was probably a smart move in this case; one can only imagine how Sinatra would have reacted in the moment to Bono’s wordless moans in the middle of the song and his changing of “little fool” to “old fool.”

Duets II followed in 1994, with Chrissie Hynde and Linda Ronstadt among the notables. Hynde brings the right amount of take-no-crap attitude to “Luck Be a Lady,” but Sinatra, closing in on 80 years old, is still the stronger and more convincing singer. Ronstadt, however, matches Sinatra’s vocal grace and tenderness on “Moonlight in Vermont,” and the warmth between them at least gives the impression they could have been face to face when laying down their parts.

The Rock and Roll Hall of Fame debate

Never mind trying to define what is or isn’t rock ’n’ roll. And don’t bother arguing that Sinatra only sometimes sang rock songs that were rearranged to suit his musical style.

It really comes down to this: Hank Williams, Les Paul, Woody Guthrie, Bessie Smith, Dinah Washington, Howlin’ Wolf and Billie Holiday are among the artists from other genres who are in the Rock Hall as early influences.

A spot for Francis Albert Sinatra is long overdue.

— By Chris M. Junior

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