Miley Cyrus Drops Surprises in ‘Hannah Montana’ 20th Anniversary Special

Two decades later, Miley Cyrus is looking back at Hannah Montana with a mix of nostalgia, laughter, and a little bit of gossip. What started as a show about a teen living a double life turned into a full-on cultural moment, and now Cyrus is finally sharing the behind-the-scenes stories fans have been waiting for.

The series first premiered on Disney Channel nearly 20 years ago and launched Cyrus into stardom when she was just 13. She played Hannah Montana, a pop star with a secret identity as regular teen Miley Stewart, and somehow made wigs and double lives feel totally normal.

Now, with The Hannah Montana 20th Anniversary Special streaming on Disney+ and Hulu, Cyrus is opening up more than ever before.

During a sit-down with Call Her Daddy host Alex Cooper, Cyrus dropped one of the biggest surprises. She revealed that she “secretly” dated fellow Disney star Dylan Sprouse.

"Secretly, okay, Dylan Sprouse was my boyfriend. I think he was the cutest," Cyrus divulged. "Dylan was my crush."

She shared that their dates often included his twin brother, Cole Sprouse, and their dad.

"Their dad would take us to sushi," she added. "I was into the whole culture, and it was a two-for-one. Like, bring the brother. Hello!”

Fans might remember both Sprouse twins from The Suite Life of Zack & Cody, which made the crossover even more iconic.

Another fun reveal involved Taylor Swift and her role in Hannah Montana: The Movie. Swift performed “Crazier” in a memorable barn dance scene, but Cyrus explained how it all came together.

"For that scene, get the tea kettle," Cyrus shared. "So the way that Taylor Swift ended up in the Hannah Montana movie was because this was kind of the beginning of her career, and they were looking for someone that would authentically — no shade — I guess, be performing in a barn. We both performed in the barn."

Cyrus also praised the song Swift co-wrote, “You’ll Always Find Your Way Back Home.”

"She ate with that one," Cyrus concluded.

Cyrus also got real about her early relationship with Nick Jonas and how it affected her tour decisions.

"Literally, the reason that the Jonas Brothers were on tour with me was because Nick was my boyfriend, and I wanted to not leave my boyfriend," Cyrus spilled. "So I'd be like, 'Okay, well, I'll go on tour if my boyfriend can come.' And they're like, 'Cute, have your boyfriend open for the show.' Boom."

That decision helped boost Jonas Brothers during their early rise, and fans got unforgettable performances like “We Got the Party.”

Cyrus didn’t stop at relationships. She also admitted to having a crush on her co-star Mitchel Musso.

"I thought Mitchel Musso was really cute," Cyrus recalled. "It's all about Mitchell now. I was like, 'Great! Crush. I'm good now. I'm set up.' "

She also mentioned developing a crush later on Zac Efron, who she got to know during the height of High School Musical. At the time, he was dating Vanessa Hudgens, which made their hangouts feel even cooler to her.

Selena Gomez also appeared in the special and reflected on her time playing Mikayla, Hannah’s rival.

"I remember being in that blue, weird makeup," Gomez said of her costume. "I remember feeling ugly in that. Because we’re, like, 15 and I want to feel pretty, and I'm like, 'Ugh.' "

The two laughed about their characters’ rivalry and made it clear that in real life, things are all love.

One of the most touching moments came from Chappell Roan, who met Cyrus for the first time during the special.

"I’m so grateful that I get to be a part of this. I mean I grew up watching Hannah at my grandparents’ house and it just means so much,” Roan said.

She added, "What I do onstage or where I can go on a red carpet and just be ... that’s because you took a lot of the heat for that in 2012, 2013. I don’t have to deal with that as much because the world took it out on you."

Roan told Cyrus she "literally walked so I could run," recognizing how Cyrus handled growing up in the spotlight.

Beyond the stories, Cyrus also returned to her Hannah Montana roots by performing classic songs and debuting a new one called “Younger You,” dedicated to her younger self.

"It’s been an honor to celebrate 20 years with Hannah Montana, and I’ve looked back at every memory with a heart full of love. Hannah, she gave me my start, but my fans gave me this life," she concluded in the special.

After all the secrets, laughs, and throwbacks, one thing is clear. The Hannah Montana era may be in the past, but its impact is still going strong.