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‘Hannah Montana’ Understood the Internet Before We Did
“It has become increasingly impossible to tell where our Hannahs end and our Mileys begin,” writes Sascha Seinfeld.
My generation grew up watching Miley Cyrus defend her private life from her public identity. Then social media made that very dilemma our own.
By Sascha Seinfeld
03.27.26 — Things Worth Remembering
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Hannah Montana—the Disney teen comedy starring Miley Cyrus as a homegrown high schooler living a secret life as a golden-blonde pop star—premiered 20 years ago this week.

The premise was simple: A teenage girl constructs a second, public-facing identity to preserve her authentic self. For 8–12-year-old girls like myself, it was as fantastical as it was captivating.

The show gave us scenes we could only dream of: your crush parachuting out of the sky in a tuxedo to profess his love for you; a rotating closet; a choreographed dance number to get your class out of detention; and a glittery Y2K Malibu Barbie lifestyle. And at the center of it, a girl with enormous energy, a Tennessee twang, and a face so warm and expressive you couldn’t look away. Every line was delivered as if the director had just said, “Now for this one, go as big as you can.”

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Sascha Seinfeld
Sascha is a writer and junior editor at The Free Press. While at Duke University, her sketch “O-Week” appeared on Inside Amy Schumer and contributed to a Writers’ Guild Award-winning season. She later worked for screenwriting duo Lauren Blum and Rebecca Angelo (Business Affairs Productions), pitching ideas for projects including Dumb Money (2023). After graduating, she wrote, directed, and fundraised for her short film The Final Cut (2024).
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