Whitney Whitney finds inspiration in unexpected places, from personal experiences and fictional characters to something as simple as a pair of socks.
Following a two-year struggle with vocal challenges, the singer-songwriter made her Lollapalooza debut in 2026. We chatted with her about her songwriting process, the stories behind Lucky and Sherry Wine, and what comes next.
We chatted with Whitney Whitney about her creative process, the inspiration behind Lucky and Sherry Wine, and what listeners can expect next.
Finding Inspiration in the Unexpected
For Whitney, Lucky began with an ordinary moment that quickly developed into a song. The experience reflects her spontaneous approach to songwriting and her willingness to explore ideas wherever they appear.
“Lucky” has an interesting story behind how it came together. When you look back at its earliest version, what changed the most before it became the song we hear now?
I definitely think how “Lucky” came together is the most random and funny story of my project. I was wearing a sock with The Starry Night on it and thought, “I wonder what inspired Van Gogh to create this painting.” I then started singing a cappella in my apartment, which ended up being the verse. The next day, I brought it in to my producer RISC and co-writer Cleo Tighe, and we wrote and recorded the whole song in one sitting. So honestly, not much changed from when we first wrote it to what you hear now.
Is there a detail in “Lucky”—whether in the writing or production—that feels important to the song but might be easy to miss on a first listen?
We did the first verse and the outro in a “live” way. RISC played the piano while I sang in the same room to give it a more intimate feeling. We didn’t even record it to a metronome.
Beyond spontaneous inspiration, Whitney often uses songwriting to process personal experiences. She approaches writing as a form of journaling, allowing her emotions to take shape before adapting them into melodies and lyrics.
You’ve compared songwriting to journaling out loud. Does knowing that other people will eventually hear those songs ever change what makes it onto the page?
Honestly, sometimes yes! Not because I’m embarrassed to say everything I feel in a song, but rather because I always want to find a balance of “good” lyrics and real story. But sometimes I find myself journaling for fun with no intention of making it into a song and thinking, “Oh, well, if I ever did want to use this in a song, it has to be said better.” And I have to stop that train of thought a lot because journaling just to express feelings should just be for me and the page when I’m not in song mode.
When a song starts from something personal, at what point do you stop thinking about the experience itself and start thinking about what makes it work as a song?
It depends. When I’m alone and know I want to turn a personal experience into a song, I’ll write a longgg poem about the experience and feeling. Then I bring it into the writing session and pick it apart to fit the melodies I come up with. I’m okay with losing a few details of the personal experience to make it work for the song.
And then when I come into a co-writing session with a personal experience that I have not put into poem form, I start telling the story to the people in the room and let everyone interpret it into lyrics with me. But if something anyone throws out really doesn’t line up with what I went through, I’ll absolutely steer it into the right, truest direction.
Experimenting With Sound
Whitney’s creative process extends beyond traditional songwriting. Rather than committing to one genre, she incorporates different musical influences while maintaining a sound that feels authentic to her.
Your music pulls from different genres without settling neatly into one. When you’re working on something new, how do you know when an influence fits versus when it starts pulling the song too far away from you?
I love not being fully tied down to an extremely specific sound. Sometimes it does go too far! But I feel like I just know immediately if something is me or not. I’ll never let something in a song stay that I don’t resonate with.
Are there parts of your taste that haven’t really made their way into your own music yet?
I want to say that I’ve explored every general thing that I’ve been inspired by! But the public has definitely not heard it all. My fourth and final EP of my project will definitely give a glimpse of some of my other tastes.
Collaboration also plays an important role in shaping her music. Whitney values honesty in the studio and approaches each session with an openness to new possibilities.
When you experiment with a new sound, what makes you decide it belongs in a Whitney Whitney song rather than being something interesting that ultimately stays on the cutting-room floor?
I feel like I just have a knowing with my main collaborators in the writing room. Like, we will be so honest with each other about whether we like what’s happening, if we don’t, or even if we see something we write being better for another artist.
Returning to the Stage
Whitney’s Lollapalooza debut marked a significant milestone in her career. After experiencing vocal problems that prevented her from singing fully for more than two years, she returned to performing in front of a festival audience.
A festival set gives you a limited window to reach people who may be hearing you for the first time. How did that shape the way you approached your Lollapalooza debut?
I was so truly honored to be asked to play Lollapalooza. I was the smallest artist on the lineup and was nervous that not a single person was gonna show up, so it made me extra driven to reach people in that limited window.
And on top of that, super fun fact, I lost my voice for over two years due to some crazy vocal problems. Lollapalooza was actually my first show ever as Whitney Whitney and my literal first time singing full out in years. So, I decided to lean into the fact that I was the smallest artist on the lineup and that I hadn’t sung for two years. It became my marketing for before, during, and after the show.
I put up custom door hangers with my name, QR codes to my music, and set times on all the hotel doors at the closest hotels to the festival, and even made shirts that said “I saw the smallest artist on the Lollapalooza lineup 2026” and gave them out to anyone who wanted to say hi to me after. Was so fun, and it definitely resonated with people.
I also really wanted to make the show itself memorable and entertaining, assuming most people in the crowd wouldn’t know who I was. A lot of my music is very orchestra-heavy, so I had a violinist and cellist on stage, which was so cool. I styled everyone in the band in a very Whitney, mismatched way, played piano for a few songs, and just sang my heart out. And then the coolest thing, which was completely unplanned, was that a literal frog jumped onto the stage during my set. Insane. Only would happen to me lol.
Catch a glimpse of Whitney Whitney’s Lollapalooza debut below.
With her return to live music, Whitney looks forward to discovering how audiences connect with her songs and how those experiences might influence future performances.
Have you ever changed something about a song after realizing that a crowd was responding to a completely different part of it than you expected?
I haven’t really been in a position where this has happened yet, but I feel like in the future, if people started responding to a different part of a song than I expected, I would totally think about changing it and probably try some things out just for fun. I think it would be really interesting to see where people connect with a song in ways that I didn’t necessarily anticipate.
Is there a song that has become harder—or easier—to perform as more time has passed since you wrote it?
Well, since I just started singing again after two years, I haven’t actually been able to perform any of the songs! But when I recorded this whole project, I was in such bad vocal pain that I have to assume every song will be much easier to sing now than when I wrote it.
Her experience with vocal difficulties also inspired an unfinished song that she hopes to revisit now that she can sing again.
Is there an idea you’ve wanted to build a song around for a while but haven’t figured out how to approach yet?
Yes! My vocal issues caused me to stay in complete silence for months at a time, and whenever I did talk, it would hurt so bad. No one ever fully understood what I was going through.
So, on one of my talking days, I recorded spoken verses of everything I had been feeling and mentally going through. It’s the saddest thing ever lol. And on that day, I decided that once I’m healed, I would only then write and sing the chorus.
I can finally do it! I have no idea what it should say or feel like. It’s the hardest thing I’ve ever gone through, so I won’t just accept a mediocre chorus. I’m nervous and excited to figure it out!
(Oh, and one day I want to write a love song to my cat Tuna)
Watch the official music video for Sherry Wine below.
The Story Behind Sherry Wine
Whitney’s latest single, Sherry Wine, introduces a fictional character who represents an idealized version of femininity. The song explores the relationship between admiration and jealousy through imaginative storytelling and elaborate orchestral production.
What came first with “Sherry Wine”: the character or the story around her?
Sometimes, as a side quest, I write K-pop songs to pitch to artists. A certain group wanted lyrics that revolved around things like “sugar, sweetness, candy, etc.” so I was thinking of words in that realm and wrote down “Sherry Wine” as an idea. I was writing by myself at my apartment, and as the song developed, I kept coming back to the phrase and thinking of cool ways to use it. I eventually thought, “Wait, that could be a name…” and stopped writing the K-pop song to do a word dump/poem in my notes about a girl named Sherry Wine. I turned her into the epitome of a perfect woman that every man would be obsessed with and every girl would envy. She’s not even real, and I’m still jealous of her lol! So yeah, Sherry Wine literally spawned from a K-pop song.
Sherry inspires both jealousy and admiration. What interested you about putting those feelings together?
I feel like everyone, or maybe just me, has this ideal version of who they eventually want to become. For me, Sherry is almost that version of the woman I’d love to see myself as, but she’s always just a step out of reach. The jealousy and admiration work together in my mind as a push to keep getting cooler and hotter lol. Sherry is just perfect, which naturally leads to both jealousy and admiration. She honestly inspires greatness!
How did “Sherry Wine” change from the original poem to the finished song?
We didn’t change much, which was super cool to me. I recorded the roughest, most cringe voice memo of the chorus melody and lyrics in my apartment a cappella, went into the studio the next day, played it for my producer Alex Wilke, and just said, “Trust me,” even though it genuinely sounded hilariously bad. Every word from the original poem made it into the final version in one way or another!
What made you want to tell this story through a fictional character?
I love making up stories for songs because sometimes my own life is boring. I don’t have anyone in my life who sparks the feelings that come up in the song, so creating a fictional character like her was a fun and new idea to explore.
The song’s production plays an equally important role in establishing Sherry’s larger-than-life personality. Working with producer Alex Wilke, Whitney developed a dramatic orchestral arrangement to capture the character’s presence.
How did the production help bring the personality of “Sherry Wine” to life?
I really wanted the production to feel like this girl was walking into a room and everyone stopped what they were doing to stare. To create that feeling, I wanted to have the craziest strings I’ve ever done in a song to emphasize Sherry’s power. Alex Wilke and I put together this mish-mosh of a wild orchestra that we didn’t think was going to work, but somehow it did, and it’s my favorite part of the song now.
Was there anything about the song that changed once you actually heard it fully produced?
This happens to be one of the tracks where we finished about 90% of the production in one day! The only thing that really changed was that when I first wrote it, my voice was in so much pain that I couldn’t record a solid vocal until way later. I was super nervous to record it because the post-chorus is so high, but I did it, and I love how it ended up!
What do you hope listeners pick up on after spending more time with “Sherry Wine”?
I hope people pick up on how I blended classic Elton John-adjacent vibes with a sort of fresh, modern take. That’s my goal with a lot of my songs: taking something that feels classic and putting my own, unexpected spin on it.
What’s Next for Whitney Whitney?
Beyond Sherry Wine, Whitney continues developing a 16-song project divided into four parts. While the earlier installments introduce different sides of her musical identity, she plans to explore a more upbeat, pop-oriented direction in the final release.
Looking at what you’re creating now, is there anything listeners might be surprised to hear from you next?
Very much so. My album 1 is a 16-song project that is coming out in four parts. The first three parts are almost all out, and the final part is surely going to come as a shock for people. It’s definitely the most pop and upbeat.
It still totally is Whitney Whitney, but it’s definitely a bit of a left turn 🙂
From imaginative storytelling to elaborate orchestral arrangements, Sherry Wine captures Whitney Whitney’s willingness to experiment while staying true to her creative instincts. Visit her official website to explore more of her music and keep up with her latest projects.