Why Not? The Most Iconic Hilary Duff Moments Of All Time

She’s baaaaaaaaack! Our Y2K overlord and savior, Hilary Duff, is blessing us with new music just when we need it most. She’s dropping her sixth studio album, Mature—because, yes, that’s exactly what she is now. From crimped hair, oversized cardigans, and keychain-worthy accessories to being a mama to her gorgeous kids, how does she even find the time to sing?! Step aside, Taylor Swift—someone’s coming for your crown.

To celebrate our bestie’s triumphant return, we’ve rounded up the 19 most unforgettable Hilary Duff moments. From singlehandedly curing homophobia to her unmatched ability to laugh at herself, here’s everything we stan about this blonde icon.

19 Best Hilary Duff Moments, Ranked

1. Backstage “LOL” throw-back

We love a self-aware queen! A Cinderella Story gave us one of Duff’s best performances, packed with iconic quotes and meme-worthy moments. Personally, I still catch myself wanting to tell a mediocre straight man, “Waiting for you is like waiting for rain in this drought. Useless and disappointing.” But the absolute most memed moment? When Sam narrates as she texts “LOL.” TikTok has been living for that one.

Duff even recreated the moment in a backstage clip for Late Night with Seth Meyers, proving she’s down for the nostalgia and definitely doesn’t take herself too seriously.

2. Salmon-tinted memories

If I were in the same room as Jennifer Coolidge, I’d never stop talking about it. But Duff? She’s surprisingly low-key, only spilling the tea when a fan asked on Watch What Happens Live with Andy Cohen. Her favorite memory? Rubbing raw salmon on Jennifer’s face while rambling about omegas. Honestly, peak Duff energy. Bonus cuteness: she says her little boy later did something similar, giving her a total nostalgic flashback.

3. Throwback Thursday

Duff posted a nostalgic photo collage on Instagram, pairing her childhood role as Wendy in Casper Meets Wendy with a modern filtered selfie, giving us all the early-’90s teen-fangirl vibes. She looks gorgeous, and honestly, it just proves she knows her roots — still Hilly from the Block. But girl, we need the link for that hat, xoxo.

4. She looks good with a mustache

Duff admitted she got a little bored by the end of her first pregnancy, but girl, she kept herself busy. She made a hilariously over-the-top spoof for Funny or Die called Hilary Duff’s Pregnancy Secrets, complete with a fake mustache, beard, and back hair to dramatize the weirder side of waiting for a baby. It even advertised a fake product, NoGrowActive, which promises to remove all extra body hair. Not gonna lie — I could use a dose for my chin. Hook me up, Hil!

5. Why not? Why NOT?!

The way I can recall every single lyric to this song but can’t remember if I turned off my curling iron—no, wait, did I? This music video is literally the magnum opus of Y2K. I’m talking bedazzled collars, zebra-print wallpaper, and a full-on dance ball that somehow feels both chaotic and elegant. She struts through it all like she owns the early-2000s, totally unapologetic, and I am so here for it. Honestly, it’s the perfect mix of “yes, this is iconic” and “how did we survive this fashion era?” Hilary just gets it: glam, fun, and zero apologies.

6. The 2007 dance

Duff is always in on the joke. Take her 2007 With Love dance on the Tonight Show: she was brunette, all in black, and giving absolutely nothing—but that was literally the TREND back then, dancing like your limbs were made of cement. Obviously, TikTok discovered the clip and went wild. I may or may not have attempted to recreate it myself. Naturally, self-aware queen Duff later recreated the entire routine for TikTok, fresh-faced with wet hair, and we are so obsessed. Even better? Her caption claimed she only did it so people would stop texting her. Iconic.

7. Hilary acknowledging other celebs

Okay, technically this isn’t something Duff did, but she’s still too cool not to include in our favorite Hilary Duff moments. One Halloween, Sophie Turner and hubby Joe Jonas dressed as Isabella and Paolo from the Lizzie McGuire Movie, with Turner’s The Staircase co-star Olivia DeJonge as Lizzie. Duff gave them the ultimate seal of approval by commenting, “IM SCREAMING.” Same, bestie, same!!

8. La la la

Raise Your Voice is literally our spirit animal. It’s all of us recording ourselves on our Nokias, fully convinced we could secretly sing, thinking we were ready for American Idol before we even knew what a vocal warm-up was. It’s photo booth videos of “Jar of Hearts,” headphones tangled, dramatic lighting, pretending we were auditioning for some high-stakes teen musical. And in this clip? Duff’s character Terri is doing scales in the classroom… and then totally shows off, proving she’s not just a teen drama star, she’s a full-on vibe. The confidence! The sass! The “I was born to own this moment” energy! Honestly, watching it now, it’s peak early-2000s magic, and we are so here for it.

9. She is a genuinely good person

During the Los Angeles wildfires, Duff and hubby Matthew Koma showed major heart eyes energy by welcoming Mandy Moore’s family into their home! Moore’s brother-in-law, Griffin Goldsmith, revealed on Instagram that the This Is Us star, her husband Taylor Goldsmith, and their kids were all staying with the couple. Absolute legends.

“Our dear friends @matthewkoma and @hilaryduff thought it wise to set up a gofundme for us to help with everything moving forward,” the musician, who also lost his home, wrote. “Not to mention they are currently housing my brother’s family. They’ve taken care of my entire family from the moment this began. I will never be able to thank them adequately.”

10. Butt tattoo

Sure, your husband might take out the trash or buy you flowers… but does he have your name tattooed on his ass? Well, Duff’s hubby does!! Koma showed off the cheek-y tattoo—just the word ‘Hilary’ in cursive—on Instagram, captioning it: “Good luck winning a fight with your wife when her name’s tattooed on your butt cheek.” Hubby goals, honestly.

11. Method acting as Kelly

No, you don’t get it — Duff didn’t just act in Cadet Kelly, she lived it!! To prep for her role as the girl sent to military school, she actually did a full month of military training. And the payoff? The movie went on to become Disney’s most-watched program in its then 19-year history!!! Get this girl an Oscar already.

12. Duff cured homophobia

Who can forget when Duff singlehandedly rid the world of homophobes?! In October 2008, she starred in a public service announcement for The Think Before You Speak campaign by Ad Council and GLSEN, aimed at stopping teens from casually throwing around anti-LGBTQ+ slurs like “That’s so gay.” And honestly? This PSA has gone full meme status over the years. Clips of Duff earnestly speaking straight facts have been recycled on TikTok and Twitter, captioned with everything from “mood” to “she really said it.” Gay men and queer kids alike have been worshipping her ever since.

13. The Gossip Girl threesome

Little known fact: Duff actually turned down a role on 90210 because she didn’t want to get boxed in as a teenage show girlie—well, more than she already was. But she later accepted a guest spot on Gossip Girl, playing Olivia Burke, a famous actress attending NYU with Dan. She even snagged a Teen Choice Award for Best Television Female Scene Stealer for her appearance. This role came with unforgettable moments, like the tragically cringe Lady Gaga jukebox musical about Snow White and the Seven Dwarves—let’s not talk about it. But the truly iconic moment that lives rent-free in our heads? When she had a threesome with Dan and Vanessa. Absolute legend energy.

14. Little Lies

Girlie starred in Younger, the show about a 40-year-old woman pretending to be 26 to score a job in publishing. Duff played Kelcie, an actual young, hip 26-year-old, who was basically the literal definition of cool. But let’s be real, the iconic moment isn’t her acting, it’s her singing. In January 2016, Duff dropped her cover of Fleetwood Mac’s Little Lies to coincide with the second season of the series, and honestly? That’s all we remember. Fleetwood Mac + Hilary Duff = eargasm.

15. No PG.

The world rejoiced when it was announced that Lizzie McGuire was coming back—adult Lizzie, finally! But the fairy tale quickly hit a snag when Duff revealed that Disney+ had slapped a PG rating on the project. Girl said that restricting it like that would be a total disservice to fans and suggested moving it to Hulu instead. Sadly, the dream didn’t last: on December 16, 2020, she confirmed the revival had been officially scrapped by Disney+.

Basically, Duff wanted Lizzie to get railed and refused to settle for less. Amen.

16. Protective Mama Bear

Duff is so vocal about her disapproval of paparazzi photographing children. She’s repeatedly called out photographers for snapping pics of her kids, and honestly, we stan a mom who fights for her family. In February 2020, she posted an Instagram video capturing a confrontation with a photographer at her son’s football game. In the clip, she told them straight-up: “I’m asking you human to human, as a mother, if you don’t know anyone here, can you please stop taking pictures of our children playing football this morning.” We ride at dawn.