Nancy Sinatra: ‘My advice to young people is don’t get married so young. Have an affair’

The Sixties icon is Hollywood royalty but she rarely gets given the credit for paving the way for women in pop. She talks to Kate Hutchinson about regret, about the art of reinvention, being shunned by Stevie Nicks and driving a hard bargain with Hugh Hefner

Nancy Sinatra: ‘I was shunned by other female artists' (Ron Joy/Boots Enterprises)

Nancy Sinatra was thrilled to see the back of Donald Trump last week – even as his getaway helicopter ascended to her father’s most famous tune. “It doesn’t matter,” the singer says, that the disgraced former president used “My Way” as his swansong. “It’s not my favourite; it wasn’t my dad’s either. It’s a terrible song.” Trump had tried to co-opt it since the beginning, she adds; that move was nothing new. But perhaps the song was, in a way, prophetic. “When he first used it I remember saying ‘and now the end is near’ is a perfect, perfect first line for him,” says Sinatra. “It took a little longer than I’d hoped – but it ended.” 

But enough airtime for him now. Sinatra, whose Twitter feed is a constant stream of enthusiasm for the Democrats and especially Kamala Harris, is taping Biden’s latest speech as she talks from her home in Palm Springs, her coiffed blonde mane as much a Californian mainstay as the flush of pink bougainvillea that’s just about visible out of the window. She wants the new president to first address “the land that’s been given away to oil companies” in America, as well as “racial injustice”. 

“I mean, that just boils my blood,” she says. “It was time for Black Lives Matter. I almost was part of the demonstrations, but at my age it’s difficult for me to march like that.”

Sinatra is 80 now, and this year begins with a flurry of reissues on the hip label Light in the Attic to celebrate her career, starting with a compilation, Start Walkin’. She’s put out old music many times before, but this campaign invites her musical legacy to be cast in a new light – there’s a sense that she hasn’t been given the same recognition as the legends in the Rock & Roll Hall of Fame. This is Nancy Sinatra, after all, who shimmied onto the global stage with a song about traipsing over men in a pair of boots, a flush of female empowerment that raised hemlines across America. Nancy Sinatra who cut countless peerless tracks with producer Lee Hazlewood – swirls of peachy psychedelia, outlaw country, and strings that appeared to sweep across ocean roads – that have been used in Tarantino films or covered by Beyoncé. She made films with Elvis. She sang one of the great Bond songs. She is a stone-cold showbiz legend.

Her influence criss-crosses the decades, too. In the Nineties, Sinatra found fans among indie-rockers like Kim Gordon, Kim Deal and Beck. Then in the mid-2000s, a revival spearheaded by her daughters, Angela and Amanda, out came a compilation of Sinatra duets with the likes of Jarvis Cocker, Bono and Morrissey. Others will remember the omnipresence of that Audio Bullys remix of her Cher cover, “Bang Bang (My Baby Shot Me Down)”. Or her cameo in The Sopranos. Her Factory Girl of the Canyons look – PVC knee-high, white boots, relaxed beehive – was mimicked by the “fembots” in Austin Powers. A decade later, you have Lana Del Rey saying she styled herself as a “gangsta Nancy Sinatra”, country princess Kacey Musgraves covering her songs, and Angel Olsen referencing her dramatic orchestral arrangements.

Sinatra also had one of the best pop reinventions in living memory, a proper Sandy-in-Grease “fluff-to-tough” moment that put the attitude in pop way before Madonna (although Black artists were, of course, doing it way way before that). When Sinatra started out as a singer in 1961, under the watchful eye of her father, she released a string of bubblegum singles on his Reprise label that failed to ignite her career. She’d married fellow singer Tommy Sands, took a backseat to his stardom, and almost got dropped. But her father teamed her with eccentric and seasoned record maker Lee Hazlewood – 11 years her senior and with a handlebar moustache that almost looked stuck on – who’d been behind Duane Eddy’s twangy rebel rock’n’roll. He convinced Nancy to drop her vocal register to something sultrier. And, well, pervier. “Like a 14-year-old girl who f***s truck drivers,” he told The Guardian in 2002. Although Sinatra was savvy about it. There was no more “Nancy Nice Lady”, she says – in came the Lolita purr, the leather, the stilettos and a song called “These Boots Are Made For Walkin’”.

So the story goes, Hazlewood had originally written “Boots…” for himself – charming, when you consider the lyrics. Sinatra told him as much. “I didn’t think it was attractive that a man sang the song,” she says. “I thought it was chauvinistic and mean. But with a feisty little girl doing it, it became lighthearted, almost cute. Fortunately, Lee agreed with my theory.” Released in 1965, it was a runaway hit and came with a promotional video – unheard of at the time – of Nancy and dancers in boots and tiny outfits doing the frug. Miniskirts hadn’t quite reached America by then so Sinatra, having been to London and seen Mary Quant’s thigh-baring creations, improvised with “a sweater that just covered my bum”. The song was also a terrific middle finger to her impending divorce from Sands, her brunette hair swapped for platinum blonde.

“I was just about to go through a divorce,” she remembers. “I was 24 years old and in shock and I didn’t really know who I was.” She knew one thing, though: “I was determined to change my image.” The success of “Boots…”, “when the hair, the miniskirt, all of that took off the way it did”, says Sinatra, caught her “by surprise.” But, she adds, “I was smart enough to utilise it. It all merged and molded this new person.”

That new person was a little at odds with reality: Sinatra was living at her mother’s house when suddenly she was launched into the stratosphere as a bombshell. Looking back, she wishes she’d had more dangerous liaisons to match the image. “My advice to young people is don't get married so young,” she continues. “Have an affair, which I never did. I did not have sex until my first husband. I was stupid and naive.” She laughs. “I made up for it later. I had a good time.”

By then, the Sixties were in full swing. In 1966, Sinatra put out three albums in quick succession – Boots, How Does That Grab You? and Nancy in London – that reinforced her It-girl status. It might seem like a small act of defiance now but her debut album included a slew of songs originally “sung mostly by men”, which was fairly radical at the time. “I was pretty naughty,” she says, reciting the lyrics to one of them, The Beatles’ “Run for Your Life”: “‘I’d rather see you dead, little boy / than to see you with another girl’, you know?” These were swiftly followed by 1967’s John Barry-penned Bond theme “You Only Live Twice”. Then came a duet with her dad, “Something Stupid” – something of a comeback for Ol’ Blue Eyes – which confirmed Sinatra as a star in her own right.

Then the music got darker. By 1968, she and Hazlewood had made a collaborative album, Nancy & Lee, where his sometimes unsettling baritone contrasted with Sinatra, who either channelled a twinkly-sweet hippie aloofness or a scorned B-movie vixen. You can hear it to masterful effect on their cover of Dolly Parton’s “Down from Dover” (which was memorably sampled in The Go! Team’s “Ladyflash” in 2004) and their two most celebrated duets, “Summer Wine” and “Some Velvet Morning”, covered by Del Rey and Primal Scream with Kate Moss, which suggest forgotten spaghetti westerns, sexy times in neon-lit motels, paisley print and parties in the Hollywood Hills, swimming in LSD punch bowls. Hazlewood was the cowboy to her starlet. It was in this period, says Sinatra, that she started feeling properly like herself. “I think the duets with Lee brought me to that place,” she says, “because they gave me an opportunity to perform vocally. And they weren't just novelty like ‘Boots…’. The duets were real songs to sing.”

During this time, Sinatra had a parallel acting career, memorably starring in 1966’s The Wild Angels, a sleazy biker flick directed by B-movie king Roger Corman, alongside Peter Fonda and a cast of real-life Hell’s Angels. But despite being “good friends” with the actor and having songs with Hazlewood that alluded to getting off your nut on psychedelics, she never touched them. “I wasn't a druggie,” she says. “Peter Fonda used to say, ‘Oh, come on Nance. Go for it,’” but she never did. “Part of me always said if we get caught, the headlines will be ‘Frank Sinatra’s daughter: busted’. But the other part of me just was not interested. I used to be in meetings where they would pass the cocaine around with a little bucket and a spoon in the Eighties. I was not into that.”

Still, she was there. If you’ve seen Tarantino’s film Once Upon a Time in Hollywood, that was a world Sinatra bordered. She says she didn’t go to many parties, though she did visit the Playboy Mansion and, oh, there was that one time she hung out with a certain actor-director couple-of-the-moment. “I went to one party at the house Sharon Tate and Roman Polanski had rented,” she says. “And you know what happened there...” On 8 August 1969, at 10050 Cielo Drive, the Manson Family murdered a heavily pregnant Tate and four others, marking a grim end to Sixties’ optimism. “I was lucky I wasn’t there on the night of the murders,” says Sinatra. “I missed out on that, thank God. It was devastating. I tried desperately not to think about it ever again.”

My contemporaries looked down on me. They didn’t know what to make of me

Even though she accepted the odd party invite, she says she was never fully in step with the countercultural movers and shakers of the Sixties and Seventies. “You know what’s funny,” she begins, “my contemporaries – girl singers – they sort of looked down on me. I don't think they knew what to make of me and my so-called career. They shunned me a little bit, which I found hurtful. And I didn't quite understand why they did.” The other successful women of that time were “more folk-oriented, like Joan Baez, Helen Reddy and Stevie Nicks”. And so she wasn’t part of that crowd?

“I wasn’t really allowed in,” she says. “I was at an event at the White House when it was the Clinton White House. I met Sheryl Crow and Stevie Nicks, and they gave me a cold shoulder. That was painful for me. It's like they didn't want to be friends. They just virtually ignored me. I tried to make an effort to shake hands, ‘so nice to meet you’ kind of thing, but they weren't interested.” Was there a sense that they didn’t view her as an authentic artist? “I don’t want to put words in their mouths,” she says, “but yeah, I think there was definitely some of that. I felt like an interloper.”

Being a Sinatra was both a help and a hindrance. “It always was and it always will be, even to this day,” she sighs, “because people have preconceived ideas of how I got here: nepotism.” The only way to overcome that, she says, was “success” and having “chart records”, which she did, although an upside of her family name, she says – despite the odd dodgy Hazlewood song – was that she was shielded from misogyny in the industry. “People didn't treat me the way they would treat just any girl off the street,” she explains. “They were respectful because of who my father is. So I didn't really see the ugly side.”

It’s true that Sinatra Sr did give her a record deal and then hooked his daughter up with Hazlewood but, even so, was she ever given due credit for her work? As she answers, I can’t tell if she’s smarting or not. “No, but it’s OK. I’ve always credited everybody else with my success. It’s alright. I’m used to it.”

It’s one thing to have made peace with it, but quite another for your agency to have been ignored. Throughout pop history we’ve been served the idea that the female singer is the dolly bird and the male producer is the (tortured) genius – has that been frustrating? “Well, it’s true in my case,” says Sinatra. “My producer saw the future, I think. He made it possible for me to have a huge career. I owe him that. And he had a lot of good material to work with. I mean, we did break a lot of ground. Not the glass ceiling, but close to it.”

She has said that she was “one of the first women's libbers” with regards to the feminist message of “Boots…” but says that it was accidental – the glass ceiling “was not even an expression I knew about in those days”. Sinatra says she only wrote two songs and one of them has been lost to time – but in other areas her actions speak volumes. There was the time, in 1967, that she self-produced an Emmy-winning TV special, Moving with Nancy, featuring her dad, Dean Martin and Sammy Davis Jr, to whom she gave a peck on the cheek – then still hugely taboo. “A big brouhaha occurred because Black and white people weren’t supposed to kiss, but I’d known Sam my whole life,” she shrugs. “We always kissed each other.”

Much later, she paid for a lot of her comeback album, 1995’s One More Time, by stripping off, aged 54. “There would not have been a record were it not for Playboy,” she says of the cover shoot she did that same year. “I really was determined to make another album and I didn't have any money to do it.” She was also self-releasing it, as she has done on her label Boots Enterprises, Inc with each of her albums since. “And when I asked Hugh Hefner if I could do a pictorial for money, he said of course.” Another unexpected plot twist, she adds: “We were old friends from way back.”

“I was a nervous wreck,” she says. “I was so embarrassed. But I was determined to get the money for this album. They offered me $50,000 and I told my dad about it. I said, ‘What do you think?’ And he said, ‘double it.’”

Her father Frank had lots of good advice, including that she should own her own masters – a trailblazing move that’s one of the reasons a project like Still Walkin’ can come to fruition. As an artist, “owning your own masters is the key to your future”, she explains, “because [then] you can control them, you can re-release them, or you can sell them if you want to. But they are yours to do with as you wish.”

It’s why, when she saw that Taylor Swift was fighting to do the same, in 2019, she tweeted some words of support. “I reached out to her on Twitter. I said, ‘Good for you. Go for it.’ I don’t know if she ever saw it or not, but I was trying to encourage her. When you think about it, it’s really your professional children: you created them, you birthed them, you raised them, and they should be yours.”

Sinatra’s creative communion with Hazlewood ended in the early 1970s, after a hastily made follow up to Nancy & Lee in 1971. Their musical style had faded from fashion and he abruptly left Los Angeles for Sweden. Some have speculated that it was so his son wasn’t drafted; others because of tax problems. But he betrayed Sinatra, who wanted to continue recording, whether with him or with someone he’d selected. “He just rudely packed his bags and left,” she says, adding that she doesn’t know if any of the theories about why he left were true. “He never said goodbye, never offered any reason, nothing. He pretty much broke my heart.”

In the liner notes of Still Walkin’, Sinatra mentions the “sexual tension” that made their creative partnership so incendiary but says now that nothing ever happened between them. She did, at least, consider it. “I guess there may have been a time when I thought about it,” she admits, but she “always had a boyfriend, he always had a wife and there was just never any opportunity to get together. So boring!” Is she sure that it’s not because she didn’t want to snog him with that big porno tache of his? She bursts into laughter, revealing a knowing sense of humour. “No, I thought he looked great with his moustache. When we first got together, he didn’t have that look. He had a sort of an Ivy League haircut. He was very smart, not the s*** kicker he pretended to be at all.”

Sinatra, you sense, can relate. When her career petered out in the late Seventies – one song, “Kinky Love”, was even banned by radio stations for its suggestive lyrics – she says she didn’t mind so much. “By then, I was so involved with my children that it really didn’t matter.” (Her second husband sadly died in 1985). She and Hazlewood eventually reconciled and went into the studio, making late-Seventies demos including “(L’été Indien) Indian Summer” (which appears on Still Walkin’), she says. They eventually released Nancy & Lee 3 in 2004, an album recorded in Nashville, three years before his death. “We were always trying to capture a new sound. But I was so passé, nobody was interested, I was has-been.” She pauses. “We used to say, ‘It’s better to be a has-been than a never-was.’”

In the spaces between albums and comebacks, Sinatra has busied herself with lovingly keeping her father’s memory alive. She wrote a book about him and hosted a radio show about his work. Now her daughters, Amanda Erlinger and AJ Lambert, have been doing the same for her, as the driving forces behind Still Walkin’ deciding which big hits and rarities it includes. “I’m blessed to have two kids who care about my legacy,” she beams, the Sinatra family tradition well upheld. But just in case there was any question of her rightful place in showbiz, she has a Hollywood star, too – which she did her way as well.

“I remember that they wanted to put me somewhere downtown next to my dad’s star and I said, ‘Could I please be by the Hollywood Roosevelt Hotel?’ They said, you can be anywhere you want! So I chose to be there instead. It’s not as lonely there. People walk over me all the time.”

‘Nancy Sinatra: Start Walkin’ 1965-1976’ is available digitally on 5 February and gets a physical release 26 March via Light In The Attic. There are further reissues planned throughout 2021