Growing up, we all thought Miley Stewart and Lilly Truscott were the ultimate "ride or die" duo. They shared a secret, a wardrobe, and basically every waking second of their teenage lives. But behind those neon Disney sets and the iconic blonde wig, things between Miley Cyrus and Emily Osment were way more complicated than the "Best of Both Worlds" lyrics made it seem.
Honestly, it’s one of those classic Hollywood stories that feels a bit like a gut punch when you first hear it. You want them to be best friends. You need them to be. But the reality? It was messy. It was tense. And for a while, it was actually pretty cold.
The rocky start nobody saw coming
If you go back to Miley’s 2009 autobiography, Miles to Go, she didn't hold back. She admitted that she and Emily struggled to get along during the first couple of years of filming. Think about it: you have two incredibly talented teenage girls shoved into a high-pressure environment where one is the undisputed lead and the other is the "best friend."
Miley wrote that they "tried to be friends, we really did, but it always ended in a fight."
It’s kinda wild to imagine now, but Miley actually felt a bit intimidated by Emily’s acting background. Emily had been in Spy Kids; she was a "pro." Miley was the newcomer with the famous dad. That dynamic created a natural friction. They were "sisters" in the sense that they fought constantly, but unlike sisters, they didn't have the shared history to fall back on yet.
Why things got so tense
The pressure of Hannah Montana was massive. By the time the show hit its peak, the two were spending more time with each other than with their own families. When you're fourteen and fifteen, that’s a recipe for disaster. There were reports of the families having to step in to mediate fights on set.
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It wasn't that they hated each other—not exactly. It was more about the competition that naturally bubbles up between young women in the industry. Miley was becoming a global phenomenon, and Emily was right there next to her, watching the whirlwind from the passenger seat.
But then, something shifted.
Around the third season, the ice started to melt. Miley mentioned that "somewhere in the course of trying to keep the peace and act like friends, it sort of became true." They started finding a rhythm. They developed code words. They even started pranking their co-star Mitchel Musso together.
The post-Disney drift
Once the show wrapped in 2011, the two went in completely different directions. Miley went full "Wrecking Ball," shedding the Disney skin in the most dramatic way possible. Emily stayed in the acting lane, eventually finding huge success on Young & Hungry and more recently on Young Sheldon.
For years, fans wondered if they even spoke.
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The answer was... barely. They weren't hanging out at brunch, but they weren't enemies either. In 2013, we saw a glimpse of hope when Emily tweeted, "need you back in my life, bro," and Miley hit her back with a "miss u. Hit me on DM."
It was the 2020 reunion that really broke the internet, though. During the pandemic, Miley started her Instagram Live show, Bright Minded. When Emily appeared as a guest, it felt like the world collectively exhaled. They laughed about their "baby teeth" years, looked at old photos of them in matching denim, and looked genuinely happy to see each other. Miley even called it the "reunion of the decade."
Where do Miley Cyrus and Emily Osment stand in 2026?
Now that we’ve hit 2026, the nostalgia for that era is at an all-time high. 2026 marks the 20th anniversary of Hannah Montana (yeah, feel old yet?), and Miley has already started teasing something "really special" to celebrate the show's legacy.
But here’s the nuanced truth: don't expect them to be inseparable.
- Mutual Respect: Emily has been vocal in recent years about how much she admires Miley’s career. When Miley won her Grammys, Emily was one of the first to publicly praise her.
- Different Worlds: Their lives just don't overlap much. Miley is a global music icon living a very "rockstar" life. Emily is a hardworking, critically acclaimed TV actress who keeps things more low-key.
- The 20th Anniversary: While Miley is designing a tribute project, sources say a full-cast reboot is unlikely. Emily has previously expressed that she’s moved on from the character of Lilly, though she’s always happy to celebrate the history they shared.
Basically, they’ve reached that "high school friend" stage of adulthood. You don't talk every day, you might not even have their new number, but when you see them, there’s an instant bond because you’re the only two people who know what it was like to be inside that specific hurricane.
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The takeaway for fans
If you’re looking for a secret feud, you’re not going to find one in 2026. What happened between Miley Cyrus and Emily Osment was just... growing up. They survived the Disney machine, which is no small feat.
They’ve both proven that you can move past teenage drama and turn it into adult respect. For anyone still holding out for a "Miley and Lilly" road trip movie, it’s probably best to just cherish the Bright Minded clips and the occasional social media shout-out.
If you want to keep up with their current projects, Miley’s 20th-anniversary tribute is the one to watch. It’s expected to drop later this year, and while it might not be a scripted reunion, it’s the most significant nod to their shared history we've seen in a decade. Keep an eye on Miley's official channels for the specific March 2026 dates.
Actionable Next Steps:
- Check out Bright Minded: If you haven't watched the 2020 reunion on YouTube, do it. It’s the most authentic look at their dynamic as adults.
- Follow the Anniversary: Set alerts for Miley's "Hannah Montana 20" announcements; she's hinted at re-recorded tracks that might feature some familiar faces.
- Support the Work: Watch Emily on the Georgie & Mandy's First Marriage spinoff to see how far she's come from the "blonde skater girl" days.