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Nancy Sinatra Wishes She Had More Affairs When She Was Young

Canadian online dating service Ashley Madison’s slogan, ‘Life is short. Have an affair’, has been raising eyebrows and stirring up controversy since the site’s founding in 2002. Without going into all of the ins and outs of the service, Ashley Madison’s business model centers around giving married individuals an easier way to commit infidelity. Classy, right?

While you might assume that this rather cavalier perspective on cheating is a modern phenomenon, it really isn’t. Actress and singer Nancy Sinatra, the daughter of Frank Sinatra, has been espousing this same idea for years now.

When reflecting on her story and career, the 81-year-old says that her only regret is not being a ‘bad girl’. If there’s a time machine and could go back and do things differently, not married as young as she did. And wrap in more affairs if possible.

The older generation instructs younger individuals to do quite the opposite, but Sinatra is a different perspective on life. We’ll get to that in a moment, so be sure to stick around.

Nancy Sinatra most famous 1966 transatlantic number-one hit single ‘These Boots Are Made For Walkin’. She begins her career as an entertainer starting with her November 1957 appearance on her father’s ABC variety show. She goes to television and film appearances, records 14 tracks that reach Billboard Hot 100 – ten, and become top 40.

Sinatra retires from the entertainment industry and is enjoying her golden years in her beach house in Santa Monica, California. Join Facts Verse as we take a closer look at Sinatra’s rise to fame. Discover the reasons why she wishes she is more promiscuous in her prime.

More Than Just A Daddy’s Girl

While Ol’ Blue Eyes, Frank is remarkable, thanks to his daughter’s 1966 hit single ‘These Boots Are Made For Walkin’. Nancy shows off a pretty decent name for herself.

Up until putting out that banger of a track, Nancy’s career appeared to be jeopardized by her father’s success. Frank cast an enormously large shadow, and those were some seriously large ‘boots’ to fill. Fortunately for her, Nancy’s #1 song made her world-famous.

In order for Nancy Sinatra to differentiate herself from her daddy’s looming influence, she did what Miley Cyrus did when she is trying to prove that she is more than just a former Disney brat who happens to be the daughter of Billy Ray.

Reportedly when she is recording ‘These Boots’, she sings as if she’s a “sixteen-year-old girl” who sleeps with “truck drivers”. Being a ‘bad girl’ persona she is able to be successful despite having one of the most recognized surnames.

Nancy Was Almost Dropped From Her Label

Even though she is working under the same label as her father – that being Reprise – Nancy’s very close to dropping after her first few singles failed to chart. Fortunately, things took a refreshing change for the better after she started working with producer, Lee Hazlewood. The duo’s first song together, ‘So Long Babe’ ended up becoming a modest hit and basically laid out a clear path that would allow ‘These Boots’ to become a landslide hit.

He tries to show off as a realistic country idiot, he’s an educated and talented who knew what he is doing.

There could be beauty, money, and simplicity, he requests that the musicians work on Nancy’s ‘dumb sound’. By that, he meant he wanted them to be uncomplicated – especially the rhythm section, bass lines, and guitar work.

When Hazlewood wrote ‘These Boots are Made For Walkin’, he intends to perform the song on his own. He wrote it several years before Nancy got a hold of it and thought of it as a party song.

Nancy convinces him and sings, it sounds ‘harsh and abusive’, but as she sings it, it’s a whole new vibe. When Hazlewood gets his latest songs, Frank nonchalantly tells him that the ‘one about the boots’ is the best.

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Reprise Tried To Cheat Nancy

Even though the song becomes a massive international hit, Reprise still tried to pull a fast one over on Nancy. Hazlewood, after ‘These Boots’ #1 in the world, Nancy comes over to his house crying. She said that the label didn’t pick up her option and she owe them 12 grand.

Hazlewood calls up his big-shot New York lawyer, and Reprise calls Nancy up the following day offering her $1 million.

Hazlewood calls up his lawyer and Nancy communicates with her Dad for Reprise to agree to her a new contract. Which makes sense considering the fact that she’s selling FAR MORE records than Frank was at that point in time.

Nancy Say’s “These Boots” Didn’t Represent Who She Was

Even though Nancy become an overnight success story and inspires a whole generation of women across the world. She still regrets doing the song.

In her 1985 memoir, Nancy would admit that the track didn’t seem to fit her personality. The persona that the song presented depicted her as ‘hard’, while she was admittedly as ‘soft as they come’.

When she’s in the studio recording the track, she first tried singing like the sweet young girl that she is. After giving it a go, the producers instructed her to sing it ‘Nasty’ like she wasn’t ‘a virgin anymore’.

Obviously, just like today, sex sells. That’s true even if you are the daughter of the ‘chairman of the board’.

Another Regret – Don’t Get Married Young

At the age of 20, Nancy Sinatra marry to fellow American pop singer and actor Tommy Sands in 1960. Five years later, the couple would divorce.

While she’s saying that there is nothing wrong with Sands – she sees him pretty adorable and admires his talent – Nancy admits that they are simply too young to marry.

In a 2021 interview with The Big Issue, the then-80-year-old aging star said that back in those days, if you are a ‘nice girl’ like she determines to be, and wants to have sex, then you marry. Obviously, marrying just to have sex is not really a winning formula for a successful relationship.

In that same interview, Nancy says that her number one piece of advice for young people is to not marry too young. Instead of tying the knot when you’re still a teen or in your early 20s, Nancy says that young people should enjoy their youth while they still can.

While continuing their education and enriching their lives, Sinatra says that young people should take time to have fun, explore who they are, and maybe even have an affair or two, because as Ashley Madison loves to remind us, life is short.

Nancy Wishes She Had Been A ‘Bad Girl’

Speaking with the Guardian in 2008, Sinatra said that being the daughter of Frank Sinatra was ‘more normal than you might expect’.

When she was a child, Frank was on the road most of the time traveling with his band. Nancy first lived in an apartment in New Jersey, and since Frank had yet to hit it big, she and her mother lived off very little money.

After Frank had become successful, she moved to a house in Jersey’s Hasbrouck Heights. Since the house’s windows were accessible from the street, and Nancy’s mother was afraid of her baby being snatched up by some crazy person in the dark of the night, Frank moved his family to Toluca Lake near Los Angeles where she spent the remainder of her childhood.

Despite being raised around Rat Packers and putting out that hit 1960s taboo-pushing hit song, Sinatra was by her own account ‘a good girl’. Looking back on things, Nancy wishes she had tapped into the culture of the 60s just a bit more and had the courage to be a ‘bad girl’.

Instead, she marries like she felt like she needs to and takes the ‘safe’ path. To think that she was both the daughter of one of the most famous ‘Bad Boys’ in the world and put out such a salaciously sexual song during arguably the most boundary-pushing decade of the 20th century and still ended up refraining from indulging in the excesses of the ‘free love’ generation is pretty crazy. You can hear the tinge of regret in Nancy’s voice whenever she talks about this.

Although she might have a few regrets over choices during her youth, Nancy Sinatra still has one incomparable life story. And with a net worth estimated at $50 million, she seems to have done pretty well for herself, all things considered.

Do you agree with Nancy Sinatra’s advice to young people to not to marry too young? And do you think that she would have found the same level of success as she did if she hadn’t been the daughter of Frank Sinatra? Feel free to share you thoughts down in the comments.

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As always, thanks for watching. We’ll see you soon with more videos covering some of your favorite stars from yesteryear, classic films, and beloved television shows.

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