A love letter to Amy Winehouse.

Jazz, pinup, and messy love

I’ve long felt a pull to Amy Winehouse, her music, her story. She’s an artist to her core. She let her heart and soul drive her life.

I remember where I was when I learned she passed in 2011 — I was walking to a coffee shop on Main Street in Tarrytown, NY. Four years later, I remember all too well watching her documentary in 2015, where I felt her pain a bit too fully. I fainted on my way to the restroom, hitching a ride with an ambulance on my way out of the movie theatre. And most recently, I watched the biopic “Back to Black” on my flight home from Thanksgiving in 2024.

Amy’s story

If my fantasy of Amy holds true, she was the type of person who was herself, to a fault. She loved what and who she loved, to a fault. All of that was her demise in the end, but also her legacy. What a way to live, and to go. And she brought us along for the ride through her lyrics.

I’m not going to glorify her addictions, of course. Amy was an addict, and it’s a tragic part of her story that I can’t whitewash. The same highs and lows that drove her to success in her music career, she also experienced with substance abuse. Despite a few attempts to help herself, her fame, relationships, and career made it difficult to recover before she sadly was taken by alcohol poisoning.

Addiction is an important part of Amy’s story, and it’s unfortunately the consistent throughline through various recounts of her life. The other throughlines, that I want to focus on here, are her immense talent, and her passionate, vulnerable heart.

Amy’s legacy

Amy turned her pain into beauty. She turned her heartbreaks, her observations, her mundanity into poetry, into connection. Amy’s authenticity is in jazz, pinup, messy love.

Not only did Amy wear her heart on her sleeve, she invited the world in to witness her ups and down with her lyrics and soulful voice. She didn’t hold back or let anything cloud her raw lyrics.

And when it came to her career, Amy didn’t let anyone control her path or steer her toward commercialism.

Tapping into Amy’s magic

Listening to her story, her music, it’s impossible not to tap into Amy’s magic.

If her authenticity is in jazz, pinup, and messy love, what are my symbols, my throughlines? What is my jazz, my pinup, my messy love? What will be my legacy?

I’m incredibly different from Amy, obviously. My authenticity is more about constantly balancing between dualities. I’m somewhere between softcore and straightedge, between a creative dreamer and a corporate nerd. But as far as clear symbols, nothing really feels like “it.” Maybe mine are still in the making.

I’m feeling inspired by Amy to be more vulnerable with my writing. I’ve been told my writing feels vulnerable, but I don’t think I’ve truly been baring my soul and heart like Amy. I’m inspired by her messiness. I tend to avoid being messy. I’ve had plenty of moments in life of embarrassment and regret, but my response has been to build a habit of holding back. I’ve held myself to the highest of standards for fear of repercussions.

Amy feels so raw, honest, and unleashed. Who am I when I am at my most raw and honest and unleashed? I’m not entirely sure, but Amy has inspired me to start figuring this out. I feel inspired to write poetry, but it feels particularly vulnerable. Maybe I can try it out, if only to capture those feelings, that rawness that arises in those moments of honest inspiration.

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What about you? What is your jazz, your pinup, your messy love?

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