5 Things Creatives Can Learn from Amy Winehouse

Allen Plummer
7 min readMar 27, 2016

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Tributes outside Winehouse’s home, July 2011 (CC via K Alexander)

The other night I watched Amy, the documentary of singer Amy Winehouse that won an Oscar earlier this year. It’s a phenomenal film, uncomfortable for all the right reasons. And if you’re a creative professional, you need to see it — even if you know her story. Regardless of her personal demons, Winehouse struggled as an artist; torn between her desire to create on her own terms and the demands of being a commercial artist. If you’re paid for your creative talents, you’ll relate.

About Amy

The film presents an exceptional, up-close look at her life, thanks in part to over ten hours of footage from her first manager (whom she met at the age of 16 and stayed life-long friends). In fact, any interviews of those who knew Winehouse were done via phone or voice only; the film has no new footage of interviews and relies solely on existing footage from her life, much of it firsthand by those closest to her. (Like many kids growing up with mobile devices, a lot of Winehouse’s teenage years and early adult experiences were captured even before her career took off.)

Because of this, the film gives an intimate look at her life. What starts out happy and promising turns uncomfortable as she begins using drugs and her health and mental state deteriorate. We know how her story ends but can’t look away from the tragedy unfolding before our eyes.

As I reflect on the film, there’s 5 things about Winehouse’s life that stood out to me; all of which will resonate with professional creatives.

Happiness is the work, not the accolades

As Winehouse’s popularity grew, it became clear that she felt more and more trapped in her own success. Big stages, paparazzi, interviews, and hectic schedules frustrated and bored her. In fact, at the height of her fame, she wishes she could just go back performing in small jazz clubs. While all the world was adoring her and her music was being played on radio stations everywhere, Winehouse longed for the days when she and her manager drove around the UK, playing bar after bar. She seemed at her happiest in the life of a “struggling” musician — traveling by car during the day and playing to a small crowd at night.

A romanticized notion? Yes, but for those of us who wish the world knew our name, Winehouse is just one of many cautionary tales. “Be careful what you wish for” is an all-too-true phrase, it seems.

Winehouse in happier times, via the Jewish Museum London

Refuse to let others define you

Winehouse was an eclectic individual, even at an early age. By 14, she had a pierced nose and was obsessed with jazz instead of 90’s pop music. As her talent matured, she sported a beehive hairdo and 50’s style makeup, all while regularly adding to the multitude of tattoos on display when she took the stage.

And it wasn’t just her appearance. Musically influenced by soul, R&B, and jazz, her sound was unlike anything else on the airwaves in the last decade of her life. Even her lyrics differed from other artists — after all, her most popular hit was a refusal to go to rehab for alcoholism.

In short, Winehouse listened to her own voice and refused to let others define her. Whether it was a school telling her how she should look, a record label trying to change her sound, or her manager telling her what she should (or shouldn’t) write about, Amy refused to compromise or cave to the expectations of others. In many ways, this was part of her downfall, but in terms of creativity, staying true to her voice gave her artistic integrity throughout her life.

Separate your professional and private lives

Like most artists, Winehouse drew inspiration from the pain and suffering of their personal life. Yet unlike most successful artists who go on to have lengthy careers, she was unable to separate her personal life from her professional one. (Perhaps it’s no surprise since she fought so hard to maintain her artistic integrity. Her music is who she was; Winehouse’s emotions and thoughts were on display in song for all to hear.)

Today, it’s not unusual to see two sides of celebrity; the glammed-up rocker or actor in millions of dollars of clothes, makeup, and jewelry, versus the disheveled, sunglasses-wearing, Starbucks-carrying, New Yorker out walking their dog on a Saturday afternoon. Winehouse, it seems, was one and same in both situations. Intoxicated on and off the stage, wearing the trademark beehive and makeup whether she was in front of 15,000 fans or trying to get through paparazzi to get into a car. Her personality was the same, too; that “I don’t give a f***” attitude people loved about her came through when she was asked stupid questions in interviews, as well as being booed on stage for forgetting lyrics, or dealing with those who loved her.

Given how much Winehouse put into her music, it’s easy to wonder if she had anything left for herself. It’s impossible to balance your professional and personal lives as an artist when there’s no difference between the two.

Seek out mentors

One of the saddest moments in the film occurs when Winehouse meets one of her idols just 3 months before her death. As Tony Bennett planned his second album of duets, he reached out to Winehouse and asked her to record the jazz standard “Body and Soul” with him. She accepted, and the film includes moments from their studio session. Not only is Winehouse awestruck during the scene, but working hard to perform at a level Bennett will appreciate. As she falters once or twice, her frustration begins to show. Ever the professional, Bennett offers words of encouragement and reassurance. The rest of the session goes smoothly and Winehouse seems genuinely reluctant for it to end.

As she thanks Bennett for the opportunity she blurts out, “You’re one of my idols,” and gushes over him. It’s easy to understand why, and this short scene demonstrates how Bennett was able to do something no one else could at the time — bring Winehouse back to her roots and draw out an amazing, focused performance. We see that Winehouse was clearly happy during the session, and it shows in her manner and voice. For a few short minutes we’re given a glimpse of Winehouse when she was at her best, the years of drugs and alcoholism stripped away, her talent laid bare.

It’s doubtful that Winehouse had mentors at this stage of her career, and it’s heartbreaking to see her connect with such a great talent in the midst of her last days. Not because of the session, but because of what of might have been. In that scene, Winehouse learned an important lesson from someone who had the potential to be a great mentor for her. Perhaps it was too late at that point, but what might have happened had they stayed in touch after that session?

No matter what stage of an artist’s career, mentors can be valuable guides and support. And as the film shows, sometimes they’re right in front of us and we don’t know it.

Having the right motivation is essential

By far, the most painful scene in the film is also the most bittersweet. When Winehouse won several Grammys in February 2008, she was forced to perform and accept the awards from London since her visa to the U.S. hadn’t been approved in time. Mixing broadcast footage from the Grammys with on-site footage from London, we see Winehouse’s shock and wonder as she wins Record of the Year for “Rehab.” Shortly after her acceptance speech, she momentarily celebrates with her band and friends. But as the broadcast cameras go off and she’s no longer televised, Winehouse goes backstage. One of her closest friends runs to her, asking what’s the matter.

“This is so boring without drugs,” she says matter-of-factly.

It’s utterly heartbreaking to see someone so talented reach the pinnacle of their career, yet unable to enjoy it because of their demons. In this moment, it’s clear Winehouse no longer enjoys her talent or the opportunity to perform. She’s singing out of obligation and putting on a front because her career requires it. Her motivation as an artist is gone, replaced by the understanding that her music has become a commodity to be sold and leveraged for money.

Winehouse’s refusal to compromise may have given her integrity as a creative, but the business of music had taken its toll. She was stuck creatively, and her motivation was gone.

I still enjoy Back to Black and make a point of listening to it regularly. But since seeing the film and gaining an intimate sense of Winehouse’s struggles, the album carries a different meaning. The songs sound more poignant, more meaningful. Most importantly, they now serve as aural reminders that as an artist, I need to protect myself. And nothing else in my 2,000+ collection of albums does that.

Thanks, Amy.

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Thanks for reading. If you liked this post, please share it with your connections. Hear my podcast, Head, Heart & Hustle, online or via iTunes. You can find me on LinkedIn or connect with me on Twitter at @MktrAllen.

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Allen Plummer

Digital Marketing leader. Head of Editorial & Creative Production. Podcaster @ Headheartandhustle.com. 5x author & ghostwriter. CrossFit and Goruck tough.