If you grew up in the mid-2000s, you probably thought Lilly Truscott and Miley Stewart were the ultimate friendship goals. They had the handshake. They had the secrets. They had the matching (and questionable) 2006 layered fashion. But honestly, the real-life dynamic between Emily Osment and Miley Cyrus was way more complicated than the Disney Channel scripts let on.
People still talk about Hannah Montana like it was a fever dream of glitter and synth-pop. It was. But behind the scenes, the two leads were just teenage girls thrust into a massive spotlight, and they didn't always see eye-to-eye.
The Audition That Changed Everything
Most people don't realize that the casting for Hannah Montana wasn't a straight line. Before Emily Osment ever stepped onto the set as Lilly, the show looked totally different. In the early development stages, the character was actually named Lilly Romero.
Miley Cyrus actually auditioned for the role of the best friend first.
Disney executives saw something else in her, obviously, and bumped her up to the lead. That left the spot of Lilly wide open. Emily Osment came in after Miley was already cast. She was already a bit of a veteran compared to the rest of the kids, thanks to her role as Gerti Giggles in the Spy Kids franchise. She had this dry, grounded energy that perfectly balanced Miley’s high-octane "out there" personality.
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Why They Struggled to Get Along (At First)
It’s easy to look back with rose-colored glasses, but Miley was pretty blunt about their relationship in her memoir, Miles to Go. She admitted that during the first two seasons, they really struggled to find common ground.
"Emily and I tried to be friends, we really did, but it always ended in a fight," Miley wrote. It makes sense. You have two talented, driven girls in a high-pressure environment where every move is scrutinized. Miley mentioned there was a natural sense of competition. They were different people with different vibes.
Emily was a bit more reserved, the "older sister" type who reminded Miley to read her scripts. Miley was the whirlwind.
By the time Season 3 rolled around, things finally clicked. They found a groove. They stopped trying to force a "perfect" friendship and just accepted each other. You can actually see the shift in the later seasons; the chemistry feels less like "we're acting like best friends" and more like "we've survived a decade of chaos together."
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That Ad-Libbed Final Line
There is a legendary bit of trivia from the series finale, "Wherever I Go." In the final scene, Miley says "I love you" to Lilly. Emily Osment famously ad-libbed the response: "I know."
Some fans at the time thought it was a bit of a "diva" move to get the last word of the entire series. Honestly? It was probably just Emily being Emily. It fit Lilly’s character perfectly—that slightly sarcastic, Han Solo-esque confidence. It gave her a sense of ownership over a character she’d played for years.
Life After the Blonde Wig
While Miley went on to wrecking balls and Grammys, Emily Osment quietly became one of the most consistent working actresses in Hollywood. She didn't have the "Disney crash" that so many others suffered.
She moved into Young & Hungry, which ran for five seasons. She did The Kominsky Method with Michael Douglas. And now, she’s basically the queen of the multi-cam sitcom again. Her role as Mandy McAllister in Young Sheldon was so popular it birthed its own spin-off, Georgie & Mandy’s First Marriage.
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It’s wild to think that the girl who spent years as "the sidekick" is now anchoring her own massive network show in 2026.
- Musical Pivot: Emily did the pop thing with All the Right Wrongs, but her later work under the name Bluebiird is where she actually found her voice. It's alt-indie, moody, and a far cry from "Let's Be Friends."
- Environmental Advocacy: Just recently, she joined the board of the nonprofit American Rivers. She’s been vocal about protecting waterways, showing a side of her that isn't just "Hollywood star."
The 2020 Reunion That Broke the Internet
If there was any doubt about where they stand now, the 2020 "Bright Minded" Instagram Live cleared it up. During the pandemic, Miley brought Emily on her show. They looked through old photos of Emily's "baby teeth" and laughed about their two-hour lunches on set.
They aren't "hang out every weekend" friends. That's okay. They are "we shared a life-altering experience and respect the hell out of each other" friends.
What You Can Learn From Their Journey
The biggest takeaway from the Emily Osment and Hannah Montana era isn't about celebrity gossip. It's about professional growth.
- Build your own lane. Emily didn't try to be "the next Miley." She leaned into her strengths as a comedic actress and a character performer.
- Professionalism over "Besties." You don't have to be soulmates with your coworkers to create something iconic. The friction between them in those early years arguably made the on-screen friendship feel more "real" because it had weight.
- Longevity is a choice. By avoiding the tabloid circuit and focusing on the craft (and some voice acting for Family Guy on the side), Emily ensured she'd still be a lead actress twenty years later.
If you’re looking to revisit the era, skip the "Best of Hannah" playlists and go watch some of the behind-the-scenes footage from the Season 1 DVD. You can see the exact moment where the "work relationship" starts turning into the "sisterhood" they eventually found. It wasn't instant, it wasn't easy, but it was real.
Next Steps for Fans: Check out Emily's work as Bluebiird on Spotify if you want to hear her actual musical style, and catch her current run on Georgie & Mandy's First Marriage to see how much her comedic timing has evolved since the Lilly Truscott days.