Nancy Sinatra – Boots: Nancy Sinatra’s All-Time Hits (1986)

An icon of the swinging sixties, Nancy Sinatra set a sound and an attitude which defined the emergence of mod style in America with a touch of female empowerment while becoming one of the era’s biggest sex symbols and recording artists.

This summer one of the songs that has been floating around my personal soundscape has been Nancy Sinatra’s “So Long, Babe.”  In the song, a woman assures her man, a failed singer/songwriter who was unable to make it in the LA scene, that turning his back on the industry, tearing down everything he built and leaving town for something new is a good life choice.  Although it is a song about failure and rejection it is sung without shame, without criticism and with compassion.  To say the least, the song has resonated quite deeply with me:

“I know you’re leavin’ babe,
Goodbye, so long.
I hope someday somebody
Listens to your song.
Those bright lights never ever
Spell your name it’s true.
Maybe a change of scene
Will be the best for you.

So long babe…

I know you’re leavin’ babe,
Goodbye, so long.
Pick up the pieces
And go back where you belong.
You gave them all you had
And what did they give you?
Well they gave you nothin’ babe
So give ’em nothin’ too.

So long babe…

I know you’re leavin’ babe,
Goodbye and so long.
You never made it babe,
I wonder what went wrong.
They never understood your songs,
Here’s what you do
Just walk away and leave ’em,
And let ’em come to you.

So long babe”

With her blonde hair, cat eye makeup and trademark leather boots, Nancy Sinatra became one of the 1960’s biggest sex symbols and still lights the heart fires of fans both male and female and young and old to this day.

“So Long, Babe” might not be the most famous of Nancy Sinatra’s hits, but its an important one because it is the song which put her on the Billboard Top 100 for the first time.  Released as a single in 1965, “So Long, Babe” barely made it in the US, settling at #86, while it fared a bit better in Canada where it broke the Top 40 at #38.  It’s been suggested that what hindered it from reaching a higher position was that it was released the same time as Sonny and Cher’s “I’ve Got You, Babe,” and that there just wasn’t room for two “Babe” songs on the charts.  But, after years of struggling to find a foothold in the public spotlight, “So Long, Babe,” was the first time that Nancy Sinatra was deemed a marketable recording artist in America.  More importantly, “So Long, Babe” paved a path for Nancy Sinatra’s megahit “These Boots Are Made for Walking,” and making Nancy one of the most recognizable and legendary pop culture icons of the 1960’s.

I’ve had a long love affair with Nancy Sinatra.  It started around 1986 when I saw her picture in a magazine.  I was eleven years old and at that age when a kid starts to really notice the opposite sex in a real different kind of way, and I didn’t need to hear her music to know that I found Nancy Sinatra fascinating.   I saw those provocative cat eyes, the short skirt and, m most importantly, those leather boots and I was hooked on Nan.   Even though I’d never heard any of her music, for my twelfth birthday I asked for a Nancy Sinatra record, and my Aunt Grace went to the infamous Young St. location of Sam the Record Man, which has become a part of Toronto vinyl collector lore, and got me a copy of Rhino Records’ 1986 package “Boots: Nancy Sinatra All Time’s Hits.”  With a gorgeous unused image from her photo session for her 1969 album “Nancy” on the cover, it fueled my hunger for everything Nancy, and her music lived up to the expectations.  Still a cherished part of my music collection, “Boots” was played a heck of a lot and soon I was the only kid in the seventh grade who knew all the words to Nancy Sinatra deep cuts like “Lightening’s Girl,” “Last of the Secret Agents” and, of course, “So Long, Babe.”  With the Monkees still reigning high as my favorite group, Nancy Sinatra became an unlikely second gateway key into my personal musical journey.

But, when it comes to Nancy Sinatra, pop culture critics often dismiss her success to pure nepotism.  The oldest daughter of Frank Sinatra, who at the beginning of the 1960’s was unquestionably one of the most powerful men in the entertainment industry, it is easy to make that assumption.  You can say lots about his throat hold on the music industry and for his different questionable dispositions, but one thing about Frank Sinatra was that he was a very devoted father and gave his kids the best of everything.  However, while we remember the boots, the mini skirts and the hit records, what seems to have gone forgotten in the narrative of Nancy Sinatra’s career is that it did not happen over night, and her dad couldn’t buy her the public’s affections.  In the beginning, Nancy Sinatra was a very hard sell. 

As the daughter of one of the most powerful show business figures of the 20th Century, Nancy Sinatra always knew what it was like to be in the spotlight. Nancy Sinatra, far left, at home with her family including Frank Sinatra, Nancy Sr, Tina and Frank Jr.

Being born into the public sphere as the first born child of one of America’s biggest stars, Nancy Sinatra never knew what it was not to be publicly known.  In fact, one of Frank’s most famous songs, “Nancy (With the Laughing Face)” written by Jimmy Van Huesen and Phil Silvers, was written about Nancy when she was two years old and became a staple of the American songbook.  So via her father’s fame, Nancy had always been on the public radar.  But, in terms of her own showbusiness career, Nancy made public debut in 1960 on one of her father’s most famous television specials and one of the era’s most fascinating television events. 

Nancy Sinatra in 1960 with Frank Sinatra and Elvis Presley during the taping of “Welcome Home, Elvis.” The show would mark her show business debut. Nancy would go on to co-star with Elvis in 1968’s “Speedway.”

Airing on ABC and sponsored by Timex, Frank Sinatra was the unlikely member of the showbusiness elite to host Elvis Presley’s return to American television after his discharge from the Army in a special called “Welcome Home, Elvis.”  Sinatra and pals Sammy Davis Jr, Joey Bishop and special surprise guest Peter Lawfor, hosted an hour-long song and dance show filled with sketches and performances that was to update Elvis on what he missed on the music scene while he was away in Europe, with the climax of the special being Elvis and Frank doing a mashup of “Witchcraft” and “Love Me Tender.”  Knowing the show was going to be a ratings giant, Frank brought Nancy onto the special where she did a special rewritten duet with her father of “You Make Me Feel So Young,” where she and her dad traded barbs about her upcoming marriage to actor/singer Tommy Sands.  In the special the Nancy that we would know later is nowhere to be seen.  At age 20 she was made up to resemble Jackie Kennedy with her dark hair done up and a conservable cut dress.  She sings well with her father, but she doesn’t show a lot of personality.  But, as her father guessed, the public tuned in in the millions to watch.  But, while it may have been Nancy’s showbusiness debut, all eyes were obviously on Elvi

Nancy Sinatra’s first single, “Cuff Links and a Tie Clip,” was released in 1961 and was a flop.

Studying music and voice at UCLA in the late 1950’s, Nancy dropped out after a year, but when your dad is the “Chairman of the Board,” who needs a diploma?  Nancy was signed to her dad’s label, Reprise Records, in 1961 and released hr first single, “Cuff Links and a Tie Clip” later that year but the song was a flop  A girlish pop song, cut in the same vein of Brenda Lee, Annette Funicello and Shelly Fabares, it was a forgettable and unremarkable single and the public didn’t buy it.  But that didn’t stop Nancy from releasing more singles.  Frank was supplying the best producers, arrangers and musicians in the business, and Nan was pumping them out.  While some of her records got airplay in other countries most notably Japan and Italy, the American teenager was not interested in Nancy Sinatra.

What was the problem?  Well, there are a few things that might be attributed to why America wasn’t buying what Nancy was putting out.  First was that she didn’t fit the mold of the traditional girl pop singer.  Already married when she started her music career, despite still being in her early 20’s she was already unrelatable to girls who related more with Lesley Gore and Donna Loren.  In fact, her marriage to Sands often eclipsed her popularity.  In a 1963 appearance on “American Bandstand” to promote the American rerelease of her Italian hit “You Can Have Any Boy” a clearly unimpressed Dick Clark spends more time questioning her about what Sands is doing than what her future plans are.

Despite being the boss’ daughter, Reprise Records had a difficult time marketing Nancy Sinatra in the early part of her career. Without a handle on the pop market, its like Sinatra and company didn’t know what to do with her.

Meanwhile, something was clearly off with the way Nancy was presenting herself.   While she could clearly hold a tune, Nancy’s voice didn’t seem to match the material that she was recording.  Nancy’s voice, while distinct, was not sweet nor girlish.  Furthermore, while she was attractive, Nancy had hard features.  She had a strong jaw line, piercing eyes and, as years went by, she was starting to be noticeably older than the other girl singers on the charts. 

Finally, the songs being chosen for her didn’t fit her, and they were, for the most part, dull and forgettable.  As the kids on “Bandstand” would say, they didn’t have a good beat and you couldn’t dance to them.  But Frank Sinatra famously didn’t know anything about pop music.  He could tell you what made Keely Smith or Rosemary Clooney incredible, but he wasn’t the best person to be guiding Nancy’s career. 

Nancy Sinatra with a pre-Gilligan Bob Denver in her film debut “For Those Who Think Young (1964).”

After multiple failed singles, Nancy changed gears and began acting, making appearances in AiP comedies such as “Get Yourself a college Girl,” “For Those That Think Young” and “The Ghost in the Invisible Bikini.”  Although all of them are basically forgotten today, except for the AiP fanatics who collect this stuff (which, probably won’t surprise anyone, but I do), Nancy was apparently the original choice for the lush role of singer Linda Kane in the Annette and Frankie classic “Beach Blanket Bingo.”  However, when finding out that her character is kidnapped in the film by the franchises comedic villain Eric Von Zipper, Nancy turned the role down due to the Sinatra’s real life kidnapping crisis when her kid brother Frank Jr. was held at gunpoint for ransom by businessman Barry Keenan a few years earlier.   The role of Sugar Kane would be one of Linda Evan’s first major film roles, and “Beach Blanket Bingo” would be one of AiP’s most famous films.

But there was a lot going on behind the scenes for Nan in 1965 and her career was hitting a crossroads.  At age 25 and now newly divorced, Capitol Records had had enough of allowing Frank to use their resources on more failed Nancy Sinatra singles and they told him that if something didn’t change they were dropping her from their roster.  Frank had to pull something off, and he didn’t know what to do.  But he had a long shot of who might know.  It was time to bring in Capitol’s mysterious lone gunfighter, Lee Hazelwood.

Singer/songwriter and superstar producer Lee Hazelwood. When Nancy Sinatra was about to be dropped by Reprise Records, Frank Sinatra brought Hazelwood in to recreate Nancy’s image and starting a successful creative partnership between Nancy and Lee.

Both a superstar producer and a songwriter with a fondness of Western music, Lee Hazelwood was a long shot, and in looking at everything that Nancy had done before, Hazelwood began to pinpoint the problems.  Lee knew the music industry and the market, and he had his thumb clearly on what was happening culturally on the pop scene.  Lee knew that if Nancy Sinatra was going to be a marketable recording artist that she was going to have to do a complete makeover and that meant everything – her image, her attitude, and her music.

Bringing some of his unproduced originals songs into the studio, “So Long, Babe” was picked as what would be the first of many Lee Hazelwood/Nancy Sinatra collaborations.   But when he saw the way she sang it,  Lee said that the “good girl” thing that Nancy had tried to emulate had to go.  She wasn’t sweet and she wasn’t even that young anymore.  She wasn’t a pop princess, she was a divorced woman on the edge of being dropped from her recording contract.  Perhaps Nancy understood enough of the rejection and her own career failures despite years of trying over and over again to understand the meaning to “So Long, Babe.”  It had a fresh modern sound, and just enough cynicism and bite to create something that had a sense of honesty about it which Nancy’s more manufactured singles had lacked.  Well, whatever was happening this time, it worked because when it got released the public bought it.

Although the art department seemed to skimp on the cover art for the picture sleeve, “So Long, Babe,” written by Lee Hazelwood, became her first successful hit record in America, landing her on the Billboard Top 100 for the first time.

But the Nancy we would come to know was still not quite there yet.  With her dark hair cropped short, she is barely recognizable on the poorly produced picture sleeve for the single (the lack of effort by Capitol’s art department on this sleeve shows how little was being put into Nancy by this point). But, when she appeared on an episode of “Hullaballoo” in 1965 to sing “So Long, Babe,” a metamorphism seemed to be happening. Nan was still a brunette and, while her hair and eye makeup was far more modern and stylish, she was still dressed in a conservative pant suit and, most noticeably, there isn’t a hint of her trademark boots.  But, accompanied by a quartet of male go-go dancers in tight slacks, Nancy showed a new attitude not seen by the public before.  Just like her father, she showed a bit of grit in her eye, spunk in her smile and a ton of personality.  A new Nancy Sinatra was emerging.

By the end of 1965 a metamorphism was happening, and a new Nancy Sinatra was emerging.

But, of course, it’d be the follow up that would catapult Nancy to fame.  Amongst the songs he had brought to the studio, a little thing Lee had written called “These Boots Are Made for Walking” was discovered by Nancy and soon Nancy Sinatra would be selling more records than her own father.  Nancy was about to become the best-selling Sinatra of the 1960’s and a pop culture phenomena.   

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