What You Never Knew About Amy Winehouse

Somehow 10 years have passed since the death of powerhouse singer Amy Winehouse. “To me, singing on stage is like breathing,” she once told MTV News in 2007. “I’m probably most at peace when I’m singing on stage.” While Winehouse’s enormous talent and passion was evident, tabloids sought to cash in on another narrative. The singer very publicly struggled with addiction and the fallout from her tumultuous relationship with ex-husband Blake Fielder-Civil, making her front-page fodder for years.

But now her family is seeking a chance to rewrite how we remember her. The 2021 documentary “Reclaiming Amy” attempts to reframe the singer’s story, with more focus on her upbringing, family, and, especially, her love for music. Executive producer Dov Freedman told Variety, “What the film is trying to do is kind of redefine who Amy was and she’s not defined by that relationship with Blake and that 12 months where, you know, there was a well-documented struggle with drugs.”

Here’s a look at some of the lesser-known details about Amy Winehouse’s too-short life and career.

She had a rap group as a tween

Even at age 10, Amy Winehouse was serious about music. She and a pal started a rap group called Sweet ‘n’ Sour in the early ’90s, which the singer described as “the little white Jewish Salt-N-Pepa” (via The New York Times). Winehouse admired female rappers for their swagger, and called Salt-N-Pepa and Lisa “Left Eye” Lopez influences to Interview Magazine (via Rolling Stone). “They were real women who weren’t afraid to talk about men,” she said, “and they got what they wanted and talked about girls they didn’t like.”

Winehouse was the “sour” counterpart to her buddy Juliette Ashby, both talented singers who wrote their own lyrics and vocal melodies. They became friends at age 4. “Primary school, from day one, me and Amy were drawn to each other and we both loved singing,” Ashby said in the 2015 documentary “Amy” (via Rolling Stone). The pair appeared to have a strong bond that lasted throughout Winehouse’s life. “Amy” director Asif Kapadia told Time Out that, though they didn’t speak as much as they used to after Winehouse found success in her music career, the friends still spoke on the phone.

Ashby’s stepfather was a producer and helped the girls record three songs in his studio when they were about 12. “They’re taking it really seriously. It’s not kids messing around,” Kapadia said. Sadly for fans, the tracks “Glam Chicks,” “Spinderella,” and “Boys … Who Needs Them” never made it onto an album and remain unreleased.

Her grandmother was a major inspiration in her life

Amy Winehouse had a close relationship with her grandmother, Cynthia, whose love of music and quirky lifestyle greatly influenced the singer. “It’s her grandma Cynthia who was a really huge influence on her in lots of ways,” said Abigail Morris, director of the Jewish Museum in London, to W magazine.

According to The Sunday Times, Cynthia was a musician in her own right who dated jazz trumpeter Ronnie Scott back in the day. Winehouse spent much time at her grandmother’s, and though the family wasn’t religious, they had Shabbat dinners with her every Friday. Recognizing her talent early, Cynthia suggested Winehouse attend an artistically focused school, and at age 9, she enrolled in Susi Earnshaw theater school. 

Some close to Winehouse say the star began to unravel after her grandmother died of lung cancer in 2006. “Cynthia was the one person who could make Amy behave and who she would really listen to,” Nick Godwyn, Winehouse’s manager, told The Sunday Times. Winehouse’s father, Mitch, concurred, stating, “Cynthia was more like a best friend to Amy. She kept her feet on the ground.” Winehouse famously immortalized her grandmother via her pin-up girl tattoo.

Amy Winehouse's tattoo artist won't replicate her pin-up girl ink

Amy Winehouse was covered in ink, but two tattoos were especially personal to the songstress. When asked if any had special significance by “The Interface,” she affirmed that they all did, but pointed out the ones with “real meaning”: the words “Daddy’s Girl” on her left shoulder and a pin-up of her grandmother Cynthia on her other arm. “This is what she looked like when she was young,” she said.

The story behind Winehouse’s pin-up grandma starts with her friendship with London tattoo artist Henry Hate. According to Vice, the pair met when Winehouse stopped by his shop unannounced after her album “Frank” was released. He didn’t realize who she was at first as Winehouse ripped pin-up tattoos from a book. She explained that she wanted the retro image to resemble Sophia Loren, and had him redraw it in a “cruder,” more cartoonish fashion until she was satisfied. “I didn’t realize at the time it would be one of the most recognized tattoos on the planet,” he told The Guardian.

Fans often ask Hate to replicate the pin-up tat, but for him, it’s one of a kind. “I always have to ask myself if Amy would have approved,” he said. He believes she would approve of having her autograph and double heart inked on fans, but he won’t tattoo Winehouse’s visage on customers either. “Fans sometimes come into my shop to ask me to tattoo her image. I don’t do it,” he said.

Amy Winehouse could have done a collab with Prince

Amy Winehouse caught the eye (and ear) of Prince early in her career. In May 2007, while on tour in London, the Purple One hinted that he might cover her track “Love Is a Losing Game,” MTV News reported, and when asked if he’d invite her on stage should she show up, he replied, “Absolutely.” During an interview with MTV News, Winehouse discovered Prince’s coy invite. “I’ll drop everything to do that,” she said, adding, “Now I want to find out how solid that is. I’d do it with bells on. All day long.”

But it wasn’t until September that they performed together. Per Far Out, Winehouse joined Prince onstage when he was back across the pond, singing the track while Prince played guitar. “I’ve got tears. I’m gonna have to get my shades on,” he said as the song finished and Amy exited the stage.

Prince reportedly invited Winehouse to come to his Minnesota home, Paisley Park, and record with him. Sources told allwomenstalk.com that she was over the moon about the invite. But the opportunity never came to be. Prince eventually covered “Love Is a Losing Game” with Andy Allo, according to The Couch Sessions.

How Amy Winehouse's "Rehab" came to be

“Rehab” was the single from Amy Winehouse’s 2006 album, “Back to Black,” that put her on the map. According to the official Grammys website, the song reached No. 2 on the U.S. charts and scored her a Grammy for “Song of the Year,” but how the song came about was pure serendipity.

After mutual friends linked Winehouse up with producer Mark Ronson, the two decided to record new music she was working on. Ronson recalled on The Howard Stern Show seeing her while she was entering his studio in New York. Recognizing her by her hair, he introduced himself as Mark, and after exchanging greetings, she told him she needed to go upstairs to meet Mark Ronson. “I thought you were going to be an old Jewish guy with a beard of something,” she laughed when he corrected her.

The pair clicked as they walked around New York getting to know each other, and Winehouse shared that she had past issues with addiction, noting her family had once tried to make her go to rehab. Making the talk-to-the-hand gesture, she said she told them, “No, no, no.” Ronson said he saw something immediately, replying, “There’s something catchy about what you just said. Do you want to go to the studio and maybe try and turn that into a song?” After spending 30 minutes working out lyrics and music, Winehouse came back to him and said, “I’ve got this song.” 

Inside Amy Winehouse's friendship with Bryan Adams

Musician Bryan Adams had a lowkey friendship with Amy Winehouse. During a tumultuous time in her life, she reportedly went to Adams’ Caribbean home as a refuge. A source told The Mirror they had “an unlikely friendship but Bryan has taken her under his wing, and he would be distraught if anything happened to her.” It was rumored that Adams wrote a song, “Flower Grown Wild,” about his friend’s struggles, though he later clarified to the Daily Mail that it was about the broader theme of female stardom.

Adams was private about their relationship. Though there are no public photos of the pals, Adams, a photographer, turned his lens on Winehouse in multiple shoots. “I don’t even know, truthfully, how anybody knows I know her — other than the fact I photographed her. I don’t really want to talk about it. Because it’s her business. You know what I mean?” he told The Telegraph in 2008.

The Hollywood Reporter featured Adams’ 2008 shoot of Winehouse for I-D magazine, noting that he’d shared that her personal style made her stand out: “Pin up style but covered in tattoos. It’s totally unique and I can’t wait for her to get back to the top of her game.” Winehouse was even featured in his portrait book, “Bryan Adams: Exposed,” and he tweeted that his photo ended up being the cover of her posthumous album, “Lioness.”

"Mr. Jones" was reportedly about this artist

In her song “Me and Mr. Jones,” Amy Winehouse croons about an old flame she wishes to rekindle, and fans quickly speculated that the song’s subject was actually rapper Nas, whose full name is Nasir Jones. In 2011, he told XXL that he had in fact heard the same before the song was released. “I don’t really remember if Salaam [the song’s producer], who was really close to her, who introduced us, if he told me about it or not,” Nas said. “I don’t remember right now. But, I heard a lot about it before I even heard the song.”

Some of the song’s lyrics have Easter eggs pointing to Nas that fans picked up on. For instance, Winehouse sings, “Mr. Destiny, 9 and 14.” Nas’ daughter is named Destiny, and Winehouse and Nas both share the same birthday (September 14).

Nas and Winehouse only met in person once, but it was rumored that she had a crush on him. He thought of her like a sister, he told to Genius, and wished he had gotten to know her beyond their burgeoning friendship over phone and Skype. The pair had reportedly been planning on throwing a joint birthday party in 2011, the year Amy died. “It was like we always knew we were supposed to be cool,” he said.

How Tony Bennett really felt about singing with Amy Winehouse

Legendary musician Tony Bennett has performed with just about everyone, forging a career of duets with artists from Judy Garland to Stevie Wonder. But singing with Amy Winehouse was a highlight of his long and storied career. Bennett told Desert Sun that, along with Frank Sinatra and Lady Gaga, he rates Winehouse in his top five all-time duets. “Amy was a true jazz artist,” he said. “She was completely improvisational and was relentless in exploring how to communicate a song most effectively.”

The two recorded the song “Body and Soul” together, which was a nerve-wracking experience for Winehouse. “She was very nervous to perform,” Bennett told Entertainment Weekly, “but I said, ‘You know, it sounds like you’re influenced by Dinah Washington.’ And all of the sudden, her whole life changed.”

He later wrote in his book “Just Getting Started” (per People) that he regretted not talking to Winehouse about his own struggles with addiction. “Sometimes — sometimes — someone will say something that strikes home on just the right day. I said nothing on the day that I might have had a chance.”

There's a statue of Amy Winehouse in Camden

In 2014, a statue of Amy Winehouse was unveiled in the singer’s old stomping grounds, Camden. Per Londonist, fans gathered to first see the commemoration on what would have been Winehouse’s 31st birthday at Stables Market, right by her favorite hangout, The Lock Tavern. Actor Barbara Windsor, a friend of Winehouse, said the placement of the statue was perfect. She told The Guardian, “Amy loved Camden with a passion and Camden loved her so it’s only right her presence should remain here.”

Sculpted by artist Scott Eaton, the statue has Winehouse’s trademark beehive hairdo and a Star of David necklace. Her parents, who were also at the ceremony, approved of the monument. Her father, Mitch, said, “I’ll be coming to visit it all the time. It was difficult to see the sculpture at first but I’m getting used to it. It looks just beautiful.”

Amy Winehouse launched a record label

In 2009, Amy Winehouse became a record executive. She launched a label that she named Lioness Records, inspired by a lion pendant given to her by her late grandmother. Per the now-defunct label’s website, Winehouse said, “When I was thinking of what to call the label I picked up the necklace and knew straight away that I’d call it Lioness, in honor of Cynthia.”

When it came to talent, the singer also stuck close to family. The first artist she signed was her teenage goddaughter, Dionne Bromfield. “The first time I heard Dionne sing, I couldn’t believe what I was hearing,” she said, per Female First, “such an amazing voice from such a young girl.” According to the Independent, Bromfield had previously achieved viral success on YouTube after singing Alicia Keys’ “If I Ain’t Got You,” accompanied by Winehouse on guitar and backup vocals.

Winehouse’s goal was to emulate the old Motown labels, and per Lioness’ website, “work closely with a small roster of artists she really believed in.” 

Amy Winehouse was swift in the studio

Amy Winehouse’s Grammy-winning sophomore album, “Back to Black,” upended the music world when it was released in 2006. The record was produced at lightning pace in New York and Miami with producers Mark Ronson and ‎Salaam Remi, who recounted the experience in the documentary: “Amy Winehouse — Back to Black.” “It was probably the quickest I’ve worked on any record,” Ronson said (per USA Today).

Winehouse came to her New York sessions prepared with music, but also whipped up the songs “Rehab” and title track “Back to Black” on the fly. “That first day, she wrote ‘Back to Black,’ all the lyrics and the melody, in two or three hours,” Ronson said, noting that it took about four days to record five songs. Remi spent 10 days with Winehouse for the rest of the album, reported Miami New Times.

Her producers have fond memories of working with the artist, but one particular story stood out. In the middle of recording “Me and Mr. Jones,” Winehouse snuck off to make tea. “When we’re listening back to the vocals, and halfway through the song, the tea kettle starts,” Remi said. “It’s there, on the record, and you can’t actually hear it, but it’s this high frequency.”

Her mother never met her ex-husband

Though Amy Winehouse was married to ex-husband Blake Fielder-Civil for two years, her mother, Janis, said she never met him. During an interview on ITV’s “Lorraine” (per Express), the interviewer asked Janis and Winehouse’s father, Mitch, if they had a chance to meet their daughter’s husband after the couple secretly wed in Miami in 2007. “No, no,” Janis replied, shaking her head. She went on to say that Winehouse told the family they’d have another wedding at some point, but it never happened.

The couple’s rocky relationship caused speculation over whether Fielder-Civil had a role in Winehouse’s issues with drugs and alcohol (he’s admitted to introducing her to heroin). But Winehouse’s mum doesn’t fault him for her death. “I believe the relationship between Amy and Blake was intimate and genuine,” Janis said to OK! (per Smooth Radio). “Their marriage was impulsive but it was still pure. It was obviously a complicated relationship but love was at the heart of it.”

Amy Winehouse's beehive 'do started as a joke

Like her music, Amy Winehouse’s iconic style was a mix of retro glam and gritty rock. Her towering beehive, often adorned with flowers, was a distinguishing part of her look. But she didn’t always rock the ‘hive, which started off as a gag from her hairdresser, Alex Foden. While styling Winehouse for a video, he went all out. “As a joke, I backcombed her hair massively and put an extra packet of hair in,” he told one publication, according to The Mirror. When she revealed her look to the crew, they were blown away. “Everybody went, ‘Oh my God! That is it, that is the signature look,'” Foden recalled.

Foden revealed details of Winehouse’s grooming habits and said she enjoyed pampering herself. “She loved her facemasks and she never left the house without her eyeliner on,” he recalled. “She’d bathe for hours and I would smell chocolate truffle all the way through the house all day; she would smell lovely.”

Amy Winehouse shocked everyone after this photoshoot

At the height of Amy Winehouse’s relationship with Blake Fielder-Civil, the couple had a “Sid and Nancy” vibe that was a vortex for tabloid attention. During a cover shoot for Spin magazine in 2007, Winehouse and Fielder-Civil were being shot by disgraced photographer Terry Richardson. As Steve Kandell, the cover story writer, tried to piece together an interview in the messy scene, he witnessed Richardson asking an assistant to break a mirror, silently daring Amy to do something with the pieces. Up for the challenge, she scratched, “I LOVE BLAKE,” into her skin. 

Per People, Winehouse laughed the incident off, saying, “It’s just chicken scratch.”

Kandell later reflected on the experience as the media went wild over the story, writing, “It was hard to know if we had suddenly become, via Richardson’s provocation, just another careless contributor to a media horde stoking the tabloid flames.”

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