I have been thinking about why I keep listening to both Amy Winehouse and Chappell Roan. On the surface, they have very little in common — different sounds, different worlds, different energy. But they sit side by side on my playlist for a reason. And it’s not random.
Amy didn’t try to move past the darkness. She stayed in it. She named it, sat with it, and sang straight from the centre of it. Her voice didn’t flinch. She didn’t try to make the pain poetic or redemptive — she just told the truth. And that truth mattered. Still does.
Chappell Roan feels louder, brighter — and she is. But she’s honest too, just in a different key. She’s not performing strength so much as living it out loud, even when it’s uncertain. There’s clarity in her vulnerability, a kind of rawness underneath the glitter that makes her impossible to dismiss.
They don’t cancel each other out. Amy lets me feel what’s heavy without rushing through it. Chappell reminds me there’s something on the other side — not always better, but still real.
I don’t compare them musically. I don’t need to. But when Chappell sings “Good Luck, Babe,” I hear it differently because I remember Back to Black. And I think that’s why I keep listening to both.
One stayed. One moved. I need them both.
(But the chord change on ‘Good Luck Babe’ is so talented. Sorry Amy)