Honestly, it feels like we lived through a dozen different versions of Miley Cyrus before the Recording Academy finally decided to give her the credit she deserved. For years, the narrative was about the tongue, the foam finger, or the wrecking ball. But when Miley Cyrus at the Grammys became the headline of 2024, everything shifted. It wasn't just about a win; it was a full-circle moment for a woman who has been "in the room" since she was a teenager but was rarely invited to the head table.
Then 2024 happened. She didn't just show up; she dominated the building.
The Night Everything Changed for Miley Cyrus at the Grammys
If you watched the 66th Annual Grammy Awards, you remember the hair. It was huge. It was "Barbarella-meets-Dolly-Parton" energy, and it signaled exactly how much space Miley intended to take up that night. After two decades in the industry, she walked in with zero Grammys and walked out with two of the biggest trophies in music: Best Pop Solo Performance and the prestigious Record of the Year for "Flowers."
The win for Record of the Year was particularly massive. She beat out a field of heavyweights, including Taylor Swift, SZA, and Billie Eilish. When she took the stage to accept the award from Mariah Carey—an "MC to MC" moment she later described as fated—she didn't give a safe, PR-scrubbed speech.
She was vibrant. She was funny. She was authentically Miley.
"This award is amazing. But I really hope that it doesn't change anything because my life was beautiful yesterday," she told the crowd.
It was a rare moment of perspective in a room usually fueled by ego. She reminded everyone that while a gold gramophone is nice, it isn't the definition of a human being’s worth. And then, in true Miley fashion, she ended the night by joking that she might have forgotten to wear underwear. You can't script that kind of authenticity.
A Wardrobe for the History Books
We have to talk about the outfits because they weren't just clothes; they were a timeline of her influences. Most stars pick a look and stick to it. Miley changed five times.
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First, there was the "Safety Pin" dress. A custom Maison Margiela creation by John Galliano that used 14,000 gold safety pins. It was punk, it was high fashion, and it looked incredibly uncomfortable, yet she wore it like a second skin.
Later, she swapped into a black sequined jumpsuit for her first win, then a silver fringed Bob Mackie vintage piece for her performance. That silver look was a direct nod to Tina Turner. If you saw her perform "Flowers" that night, you saw the ghost of Tina in her footwork and that raspy, powerhouse delivery. She even called out the audience during the song, asking, "Why are you acting like you don't know this song?"
She ended the night in a chocolate brown Gucci gown, clutching a bamboo-handle bag like a shield. It was a masterclass in visual storytelling. She wasn't just a pop star; she was a legend in the making.
The Subtle Shade and the Family Dynamics
While the world cheered, the internet—as it always does—started sleuthing. People noticed a glaring omission in her Record of the Year speech. She thanked her mom, Tish. She thanked her sister, Brandi. She thanked her "main gays" and her team.
But she didn't mention Billy Ray Cyrus.
This sparked a firestorm of speculation about the "Cyrus family feud." Following her parents' divorce and subsequent remarriages, the tension has been palpable. By omitting her father from the biggest speech of her career, Miley effectively confirmed that things are... complicated. It was a loud silence. In a world where celebrities often fake "all-is-well" family photos, her refusal to perform a happy family narrative felt like another layer of the "new" Miley: honest, boundaried, and finished with the games.
Why "Flowers" Was the Turning Point
A lot of people think "Flowers" won because it was a catchy radio hit. That’s only half the story. The song became a cultural anthem for self-reliance. Released on her ex-husband’s birthday, it flipped the script on Bruno Mars’ "When I Was Your Man."
Instead of waiting for someone to buy her flowers, she realized she could do it herself.
The Recording Academy loves a comeback story, but they love a "growth" story even more. "Flowers" represented the moment Miley stopped trying to shock us and started trying to move us. It worked. The song spent eight weeks at number one and became the fastest song to hit a billion streams on Spotify. By the time she stood on that Grammy stage, the win felt less like a surprise and more like a coronation.
Breaking Down the Wins:
- Best Pop Solo Performance: "Flowers"
- Record of the Year: "Flowers"
- 2025 Follow-up: She continued the streak by winning Best Country Duo/Group Performance for "II Most Wanted" with Beyoncé.
What Most People Get Wrong About Her Success
There is a misconception that Miley finally "figured it out" with Endless Summer Vacation. The truth is, she’s been this good for a long time. Go back and listen to Plastic Hearts. That album was a rock masterpiece that arguably should have swept the Grammys years ago.
The difference was the alignment. In 2024, the public’s perception of her finally caught up to her actual talent. She stopped being the "wild child" in the eyes of the voters and became a peer.
Actionable Takeaways from the Miley Era
Miley's journey at the Grammys offers a few "real-world" lessons that apply even if you aren't a multi-platinum recording artist:
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- Persistence isn't linear. It took her 20 years to win her first Grammy. If you feel like you're "behind" in your career, remember that the timing of your breakout doesn't diminish the quality of your work.
- Authenticity beats a script. Her "no underwear" joke and her refusal to thank people she wasn't on good terms with made her more relatable, not less. People crave the truth in an AI-generated world.
- Visuals matter. She used fashion as a tool to command respect and pay homage to her idols. Use your "personal brand" to tell the story you want people to believe.
- Know your value. Her speech reminded us that external validation (like a Grammy) is great, but it shouldn't be the "North Star."
The story of Miley Cyrus at the Grammys is still being written. With her 2025 win alongside Beyoncé and her continued evolution into the visual album space with Something Beautiful, she’s no longer chasing the industry. The industry is finally chasing her.
If you want to dive deeper into her discography, start with the Backyard Sessions on YouTube. That’s where you see the raw vocal talent that the Grammys finally acknowledged. It’s not just pop; it’s soul. And it's exactly why she's still the most interesting person in the room.