Surprisingly Amy Winehouse’s Recklessness, Vulnerability and Raw Integrity Manifested Her Deepest Dreams

Amy’s strong, bold and sultry voice – almost unexpected for her small, physical stature slides effortlessly from the depths of her soul – imbuing all who listen to her tunes, reminiscent of ‘girl bands’ of the 50s and 60s, with a vibe of wonderment. Amy was unquestionably unique, evident in her voice, her ability to write her own songs, as well as trend setting her personal modern day tattooed, bee-hived pin up girl style. She changed the trajectory of music for modern jazz artists in our time.

Amy’s true vocal and writing talent success and notoriety in the music industry was not dependent, like many musicians, with an emphasis on marketing, good producers and management companies. This woman achieved it on her own – ‘ditched’ her initial management company and forged her own path. Her weapon? Being reckless, vulnerable and maintaining her integrity in an effort to be uncompromisingly true to herself. This is what – without a doubt, built her connection to the world where her fans could relate to her on a very profoundly personal level.

Amy sang of what other artists would perhaps only scratch the surface of. She sang of all that was true in her own life, and the reality she lived– and would sing of nothing less.  She had the audacity to sing of being ‘the other women’ as well as her own substance addiction and great losses in love.  When listening to her tunes, one can gather that her experience certainly shaped her art and that her feelings and emotions were the catalysts. Hearing Amy’s music draws you into the reality she was experiencing at the time – and so it should.

So she was reckless and at times, came across as being adverse to authority – however, when you look at Amy’s career as a whole (minus some events in her personal life), recklessness really was her ability to keep herself focused on what she did best – composing and singing her own music at all costs and not considering or fearing the outcomes.

“She’s reckless, very determined, and if she wants to do something she will just do it. No one can stop her once she’s made her mind up, but she never thinks of the consequences.” (Amy’s mother, Janice.  Amy Winehouse – lives cut short).

This character trait of Amy’s was prevalent as a common thread woven through her school days, despite being accepted to notable schools for her talent, namely the Sylvia Young Theatre School;

“I didn’t like being told what to do. I was on report all the time…it gets to you after a while…so I left.” – Amy Winehouse

By being ‘reckless’, Amy was taking necessary action to keep herself on her path of passion.  She had a strong inner knowing on what to focus on in her life and rejected anything other than that when it came to music. Initially at the beginning stages of her singing career, Amy had a management company.  They were attempting to refine her with respect to speech (she had a very heavy English accent) and her style – which at the time was more sophisticated.  Amy couldn’t bare it (being told what to do) and fired her management company to go out on her own.  This is when the Beehive and Tatoos started to appear.  Celebrities are often heavily influenced by their managers, however, Amy had said that when you have so much going on on your own – there’s really nothing much more they can do – you have all the power.

In addition to being ‘reckless’, as mentioned earlier, Amy was able to be quite vulnerable in her music and maintained a high sense of integrity with herself as a result, demonstrated through her lyrics – which set her apart from the rest.

In an interview with a former teacher, (Amy Winehouse – the Untold Story) she was described as having a vulnerability and an integrity that all good artists tend to possess. To further this point, Amy mentioned in another interview that her writing was all based on true events and that she wouldn’t have been able to write any other way. This is what connected her to her fans and to the world. She kept it all real and was brave enough to share it – honest and raw!

Amy was open enough to sing about her own struggles with alcohol in coping with the forced separation of her and her husband Blake in ‘Waking up Alone’;

“Got so sick of crying
So just lately
When I catch myself, I do a one-eighty
I stay up, clean the house
At least I’m not drinking
Run around just so I don’t have to think about thinking
That silent sense of content
That everyone gets
Just disappears ‘soon as the sun sets”

… and admitting she would not get help for her addiction in her song ‘Rehab’;

“I don’t ever want to drink again
I just, oh, I just need a friend
I’m not gonna spend ten weeks
Have everyone think I’m on the mend”

She was honest enough to sing about the ebbs and flows of the relationship with Blake to which a divorce was eventual in  ‘Love is a Losing Game’, as song exuding nothing but despair;

“One [a game] I wished, I never played
Oh, what a mess we made
And now the final frame
Love is a losing game”

Despite the darkness Amy would’ve felt conjuring up these lyrics – despite all the bizarre acts her and her husband performed in the name of their relationship – despite rejecting and accepting rehab only to have died of alcohol poisoning in the end – we can’t deny that the words Amy sang, resonate with us at a fundamental level – so much so that it is somewhat haunting. It is almost as if Amy had to go through the addictions, the co-dependent relationship in an effort to produce the chilling reality portrayed in her music for all to experience.

“I’m a positive, happy person, generally. The songs I’ve written are about some bad times in my life.  I needed to make something good out of something bad.” – Amy Winehouse

Because all of us have the potential of trudging down a path to the dark side at one time or another in our lives – and her music beautifully articulates this fact no matter how messed up the situation is and how they truly feel.  This is how she was able to change music.

‘I think she made it possible for the other artists that come through to exist and put some truth and honesty back in music again’ (Stefan Starbek – songwriter, Amy Winehouse – Lives Cut Short)

On that note, if Amy wanted us to know anything at all – her message for humanity- her torch, perhaps would be this:

Tell them about me – tell them I’m just ordinary like everyone else – with my flaws and my darkness and demons. We all have these and some are able to live with them, cope and tolerate them more than others. We all have the potential no matter what decisions we make, no matter our personal or professional failures, no matter how long we live on this earth – all of us have a potential. It is of little importance how long we’ve lived, how we’ve lived – but rather the impact we’ve made and hopefully -despite our good or bad, living our impact on the world around us would’ve been positive and served to change things.

Ironically, years before Amy’s death, she made the following statement;

‘If I died tomorrow, I would still feel fulfilled, in a way’.. (Amy Winehouse)


  • Aretha, David. Amy Winehouse R & B Jazz and Soul Musician: Lives Cut Short. Minneapolis, MN: ABDO Publishing Company, 2013.
  • Aretha, David. Amy Winehouse – The Untold Story, Documentary Channel 5 .YouTube, 2011.

Author Bio: Alessandra Aversa

Alessandra Aversa has recently re-kindled her love and passion for writing. She is currently building up her writing profile. If you would like to contact Alessandra, her email is:\