Fenne Lily on 『Win Win』: An Album That Wraps Loneliness and Pain in Warm Sounds

Last Updated on 2026-10-22 by a-indie

How the Cover and Music Video Show Her Way of Facing Fear

─Wakiki : The artwork for 『Win Win』 is striking: it looks as though we are seeing you from inside the mouth of a creature. Is it a dog? A monster? I believe this visual also appears in the music video for 「Thank You Sorry」. Could you tell us why you chose this image for the album cover? In the video, I was also struck by how you seem to observe the creature calmly rather than running away from it.

Fenne Lily「Thank You Sorry」(Official Video)
From the 4th album 『Win Win』

Fenne : It’s a dog!
The photographer, Sage Szkabarnicki-Stuart, has a lot of animal imagery in her work and it was her idea to have a portrait of me from inside a dog’s mouth.
We couldn’t use a real dog so she built a skull and added the tongue and cheeks and saliva, it was a masterpiece.
I feel like the album cover sums up the feeling of being hunted down by something — being heartbroken or missing a person or a place does feel like you’re being chased, I think.
But also interacting with the fear takes away some of its power.
Looking at it for what it is not what it represents or what it’s done to you before or would it could do.
Pain is scary but the fear of pain is scarier.
As I get older I hope I become more able to see pain as a part of the process of loving things.

My dad gave me some great advice about loss — that there are two ways to let go, one is trying to hold onto the leaving thing and resisting, and one is watching it leave, taking it in, appreciating that you had it.
Looking at fear and pain isn’t comfortable but it’s necessary, for the next time, because there’s always a next time.

The Rawest Song, 「in Life and on Planes」

─Wakiki : If you had to choose one song from 『Win Win』 that you particularly want listeners to hear, or that best represents the album as a whole, which would it be? And why?
Fenne : The last song on the record (「in Life and on Planes」), the final and most raw piece of the puzzle.
It’s the least produced, just me and Sam, recorded to tape, both tracking together, and I feel a lot when I hear that recording.
It’s unfiltered, exactly what happened and how it felt, how I felt stupid and lost and then finally clear.
It hurts a lot to be left in the dark, it causes a lot of damage down the line — it’s hard to trust people when someone breaks that.
I feel that pain again when I hear it, I think that’s a good sign?
Choosing the least produced song on a record that’s otherwise really full means it isn’t the most indicative of the album sonically, but it feels completely true.