Featured Image Credit: Getty Images
Topics: Entertainment, Millennials, Music, Feel Old Yet?
Simone Margett
Topics: Entertainment, Millennials, Music, Feel Old Yet?
The OG Disney Princess is back! Before Olivia Rodrigo was journaling her heartbreak into Grammy gold, Hilary Duff was wandering through rainstorms in cable-knit sweaters, asking us to come clean. Millennials grew up with Hilary as Lizzie McGuire and Sam Montgomery. For us, her music wasn’t just catchy; it was the emotional background noise of our adolescent lives.
Since 2002, Duff has released five studio albums. While she first began in a pop-rock singer-songwriter role (Metamorphosis era, anyone?), she evolved into a dance-pop star unafraid to bare her soul or flaunt her confidence. Whether she was whisper-singing about heartbreak or strutting through synthy beats in heels, Hilary gave us range. Her most recent album, Breathe In. Breathe Out., was released in 2015 — and honestly? It still holds up.
And let’s be honest: part of her cultural dominance came from the fact that we were just a little jealous. She got Chad Michael Murray in A Cinderella Story, and we were left daydreaming in our geometry classes, wondering if a football-playing prince would ever text us back.
While she’s now thriving as a mom, actress, and unofficial CEO of Millennial Calm Energy™, her early-2000s discography still hits like a wave of sparkly, angst-ridden nostalgia. And with new music around the corner, it’s time we give it the chaotic, overly sincere ranking it deserves.
These are the songs that felt like therapy before we could afford actual therapy.
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Let the rain fall down and wake our teenage souls. This was the soundtrack to every dramatic middle school moment — breakups that lasted 36 hours, diary entries written in gel pen, and moody stares out rainy car windows.
“So Yesterday”
A breakup anthem for when your 7th-grade situationship ghosted you after two weeks. The lyrics were savage in that PG-13 Disney way: “You can bite me.” Iconic. Also responsible for a generation of girls cutting their own bangs because “new hair, new me” was born with this song.
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Hilary’s underrated “you got this, babe” moment.” “Fly,” said, “Yes, you’re crying over a boy who still wears cargo shorts — but you are powerful, and your future is bright.” If you didn’t perform this in your room with a hairbrush mic, were you even alive in 2004?
Her pop princess era, when Hilary put on lip gloss, danced in front of wind machines, and told the world: I’m not Lizzie anymore.
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Sexy, sleek, and — let’s be honest — a bit confusing when it first dropped. It was like our big sister Hilary showed up in smoky eyeliner, whispering, “I’m grown now.” Still a bop. Still feels like entering your early twenties even if you’re already 35.
The whistle hook alone deserves its own plaque in the Pop Music Hall of Fame. This was peak Duff comeback energy — flirty, fun, and perfect for Instagram captions about “catching feelings” (ew). Justice for Breathe In. Breathe Out. — an actually solid album that didn’t get its flowers.
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Hilary does glam city girl fantasy! You’re in a limo. You’re going to a party. You’re possibly in your early teens. None of it made sense, and that’s why it was perfect. “Wake Up” was pre-Spotify playlist mood boarding, and we owe it to our glittery adolescence.
Unfairly forgotten, but genuinely one of her best. Country-pop vibes, acoustic guitar, and a chorus that sounds like it belongs in a CW rom-com montage. If this had been released by Taylor Swift in 2012, it would’ve gone platinum.
Slightly cheesy? Yes. But they’re core memories, and we will defend them with our lives.
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Did we believe we could move to Rome, get mistaken for an Italian pop star, and duet at the Colosseum? Yes. And that’s exactly why this song lives forever. This was the height of childhood delusion, and we wouldn’t have it any other way. Paolo was trash, but Hilary carried.
This was millennial YOLO. “Why Not” was the theme song for the imaginary rules we gave ourselves as kids: eating dessert before dinner, starting a scrapbook, dyeing a pink streak into your hair with Kool-Aid. Cheesy? Yes. But necessary. Try hearing that chorus now and not feeling like you’re about to conquer middle school.
Deep Disney Channel Original Movie cut, but if you know — you KNOW. A Lizzie classic that lived in every burned CD mix and had strong I’m getting ready for the school dance energy.
Hilary Duff didn’t just give us bops; she gave us a soundtrack to growing up. Her discography is a time capsule of low-rise jeans, dial-up internet, and the messy, beautiful process of figuring out who you are. These songs taught me how to feel, how to heal, and how to seriously overreact to everything — and I wouldn’t have it any other way.