You’ll always find your way back home.

*Hannah Montana *turns 20! See Miley Cyrus and her Disney costars, then and now

You'll always find your way back home.

By Daysia Tolentino

Daysia Tolentino

Daysia Tolentino is a writer at *. *She has written for * *since 2025. Her work has appeared in NBC News, Vulture, GQ, and InStyle.

EW's editorial guidelines

March 24, 2026 11:20 a.m. ET

Leave a Comment

Miley Stewart and her inner circle in the cast of 'Hannah Montana'. Credit:

Twenty years after its premiere, *Hannah Montana* remains one of the most influential pieces of tween pop culture for both Millennials and Gen Z. Miley Cyrus played out every young girl’s dream, living a double life as normal teen Miley Stewart and pop star Hannah Montana. Who wouldn’t want to moonlight as the biggest musical sensation in the world?

The Disney Channel show has even inspired the likes of real-life artists Chappell Roan and Sabrina Carpenter. As Hannah, Cyrus perfected the playbook for crafting a persona — a skill that some of today’s larger-than-life pop divas have incorporated into their own creative canons.

In light of the show’s 20th anniversary special, let’s take a look at what the cast has been doing since the show’s finale.

Miley Cyrus (Miley Stewart/Hannah Montana)

Miley Cyrus in 'Hannah Montana'; Cyrus at the 2026 Grammy Awards.

The second Miley Cyrus graced our screens as everyday teen Miley moonlighting as a global pop singer (or is it the other way around?), viewers could feel her star power.

As the show grew in popularity, Cyrus began living the pop star lifestyle herself. Since *Hannah Montana *launched, Cyrus has released nine studio albums and won three Grammys.

“There was a time in my life when you held more of my identity in your glove than I did my bare hands,” the pop superstar wrote in a letter to “Hannah” on the show’s 15th anniversary. “We had an equal exchange in which you provided me a superlative amount of fame in return for the anonymity I could gift to you. But a lot has changed since then. You were like a rocket that flew me to the moon [and] never brought me back down.”

The Tennessee native has primarily focused on her musical career in the years since, including playing a pop star in a 2019 episode of *Black Mirror*. Elsewhere, she* *headlined the Nicholas Sparks adaptation *The Last Song *(2010) and Woody Allen’s limited series *Crisis in Six Scenes *(2016).

The singer/actress got engaged to musician Maxx Morando in 2025.

Emily Osment (Lilly Truscott)

Emily Osment in 'Hannah Montana'; Osment at the Emmys in 2025.

Emily Osment played Miley’s loyal best friend Lilly. After discovering Miley’s secret identity, Lilly adopted her own alter ego: Lola Luftnagle, Hannah’s “personal assistant.” The two were so close, Lilly eventually moved into the Stewart household after her mother’s move to Atlanta.

Osment reflected on *Hannah Montana*’s anniversary in a recent Instagram post.

“On the heels of our *Hannah Montana* 20 year milestone, our beloved *Georgie and Mandy’s First Marriage* director Mark Cendrowski brought in his old copy of an *HM *episode this morning,” she wrote. “Proves a few things. First, that I’m old, second that I’m still doing what I love.”

As she mentioned, Osment has become a sitcom leading lady in her own right, landing one of the title roles on the *Big Bang Theory *spinoff, *Georgie and Mandy’s First Marriage* (2024–present). Mandy was first introduced on the series *Young Sheldon *(2022–2024).

The rising star has kept busy since her Disney Channel days. She headlined the ABC Family comedy *Young & Hungry *(2014–2018) and had a major supporting role on the Golden Globe-winning *The Kominsky Method *(2018-2021), opposite Michael Douglas and Alan Arkin.

A definitive ranking of every 'Hannah Montana' song

Miley Cyrus says Billy Ray Cyrus protected her 'every single day' on 'Hannah Montana' set

Mitchel Musso (Oliver Oken)

Mitchell Musso in 'Hannah Montana'; Musso in 2018.

“Smokin’ Oken,” played by Mitchel Musso, was Miley and Lilly’s best guy friend. Since they were a package deal, he even got his own alias: Mike Standley III.

Oliver later fell in love with Lilly. He also created the infamous “cheese jerky” alongside Jackson while working at Rico’s Surf Shop.

“Hannah Montana wrapped around my heart and never really let go. We literally grew up with ya’ll,” Musso posted on Instagram in March 2026. “So many of you building families of your own and sharing this wonderful story with your kids is a gift beyond words. It’s been the coolest part of *HM*.”

Musso, who voiced the lead role in the Oscar-nominated animated film *Monster House *(2006), later starred on Disney XD's *Pair of Kings* (2010–2012).

The Texas native is also a singer, having released two albums, including 2022’s *Ghost*.

Jason Earles (Jackson Stewart)

Jason Earle in 'Hannah Montana'; Earles at the 'Wizards Beyond Waverly Place' premiere in 2024.

Like any good big brother, Jackson, played by Jason Earles, kept Miley humble. He didn’t care much about the pop-star fanfare. That nonchalance occasionally came back to bite him; his refusal to adopt a disguise when little sister was in pop-star mode led to tabloid rumors that he was dating Hannah Montana.

In 2025, Earles recalled that his character almost had a completely different personality.

“The original Jackson was the worst,” Earles said on the *Magical Rewind* podcast. “He was so introverted, and he didn't know how to, like, handle his sister’s success. And so his way of coping with the world was talking with an orangutan hand puppet. It was awful.”

Luckily, they didn’t need the primate and instead developed good sibling chemistry. After *Hannah Montana,* Earles continued working on Disney projects, including the martial arts-themed *Kickin’ It* (2011–2015) and the mockumentary *High School Musical: The Musical: The Series *(2022–2023)*.*

The actor married Katie Drysen in 2017, with costars Emily Osment and Moises Arias in attendance.

Billy Ray Cyrus (Robby Ray Stewart)

Billy Ray Cyrus in his 'Hannah Montana' years; Cyrus in London in 2025.

In life and on screen, Billy Ray Cyrus is Miley’s father. On *Hannah Montana*, he played Robby Ray Stewart, a former country music star who served as Hannah’s manager. Out of the spotlight, Robby was a widower and caring father to Miley and Jackson.

Despite the show’s runaway success, Cyrus has expressed regrets. He told *GQ* in 2011 that it “destroyed my family.”

“I’d take it back in a second,” he said*. *“For my family to be here and just be everybody okay, safe and sound and happy and normal, would have been fantastic. Heck, yeah. I’d erase it all in a second if I could.”

Cyrus rose to prominence as a country singer in the ‘90s, breaking through with the hit “Achy Breaky Heart” in 1992. The album, *Some Gave All*, went platinum nine times over. He’s been a regular in the studio ever since, with 16 LPs and counting.

More recently, the Kentucky native hopped on the 2019 remix for Lil Nas X’s “Old Town Road,” which spent 19 weeks atop the Billboard Hot 100 and won a CMA Award.

Acting-wise, the singer made a noteworthy appearance in David Lynch’s *Mulholland Drive *(2001) and later co-created and starred on the sitcom *Still the King* (2016–2017) as a washed-up country star.

Cyrus has six children and has been in a relationship with Elizabeth Hurley since 2025.

Moisés Arias (Rico Suave)

Moises Arias in 'Hannah Montana'; Arias at Halloween Horror Nights in 2025.

For Moisés Arias, his character’s name said it all. Rico Suave was the smooth-talking, conniving tween owner of Rico's Surf Shop. He was often a thorn in the Stewart family’s side, especially for Jackson.

The actor told PEOPLE in 2025 that the show wasn’t simply a job — it carries lasting importance to this day. “It was a time not only in the audience, like, in the fans’ lives, but in mine,” he said. “It's a feeling of growing up together.”

Arias, who first broke through on the big screen in *Nacho Libre *(2006), went on to more featured roles in the coming-of-age dramedy *The Kings of Summer *(2013) and as an infamous sci-fi bully in the adaptation of *Ender’s Game *(2013).

The New York native was part of the ensembles of *The Stanford Prison Experiment *(2015) and the award-winning child soldier epic *Monos *(2019). Following appearances in *Five Feet Apart* (2019) and *The King of Staten Island *(2020), he landed a regular gig on the post-apocalyptic hit *Fallout *(2024–present)*, *which will film its third season later this year.

Cody Linley (Jake Ryan)

Cody Linley in 'Hannah Montana'; Linley in L.A. in 2025.

Cody Linley stole hearts as Jake, a teen television star and Miley’s on-and-off boyfriend. Jake was a little full of himself, but to be fair, he didn’t have the luxury of separating his fame with an alter ego.

Jake was part of the love triangle with Miley and her bandmate Jesse, dramatized in the two-part season 3 episode “He Could Be the One.” While Jake prevailed over Jesse, he and Miley eventually called it quits.

“It was amazing,” Linley recently told *Today Show Australia*. “Miley’s always been extremely talented and vivacious. So, it’s an honor to look back 20 years later and celebrate where we’ve all come.”

The native Texan had a handful of bit parts under his belt when he was cast, including *Cheaper by the Dozen *(2003) and Martin Lawrence’s basketball comedy *Rebound *(2005).

During his *Hannah Montana* tenure, he competed on *Dancing With the Stars* (2008), placing fourth with Julianne Hough.

Drew Roy (Jesse)

Drew Roy in 'Hannah Montana'; Roy in 2010.

Drew Roy has a penchant for playing bad boys, including Miley’s edgy bandmate Jesse.

Miley flirted with Jesse to rile up her father — and make Jake look better — but later developed real feelings for him. When forced to choose between the two boys, she initially chose Jake… but ultimately wound up with Jesse.

“That was the first time I worked with someone of that star caliber, and I was surprised at how normal she was,” Roy told *Elle* in 2012. “She’s extremely talented but also has that familiar feel of a girl you went to high school with, that hometown feel.”

The Alabama native also played a bad boy crush on *iCarly *(2009–2010) and even returned for the revival series. He went on to star on the sci-fi series *Falling Skies* (2011–2015) alongside Noah Wyle.

Roy married Renee Gardner in 2015 and they have two children.

Brooke Shields (Susan Stewart)

Brooke Shields in 'Hannah Montana'; Shields at Paris Fashion Week in 2026.

Although Brooke Shields didn’t play a living character, she still had a major presence in the Stewart household. She was Miley and Jackson’s late mother, who died before the start of the show. Susan is the heart of the family, even if she’s only present in flashback memories and dreams.

In fact, the veteran actress may have even been a bit *too* convincing as a maternal figure on set. “Hannah was my baby girl. So, oh God, my daughter loved the show,” she told PEOPLE in 2025. “We brought her to a taping and I failed to explain to her that when I called [Cyrus] ‘baby girl’ she wasn't being replaced by this girl… It created a little bit of a kerfuffle.”

If anyone can relate to struggling with overwhelming young stardom, it’s Shields. The former child star went through the controversies of *Pretty Baby *(1978), *The Blue Lagoon *(1980), and her Calvin Klein jeans campaign. She addressed those years and more in the documentary *Pretty Baby: Brooke Shields, *in 2023.

As she got older, she carved out a life and career on her terms. She graduated from Princeton and made her mark on TV with *Suddenly Susan *(1996–2000), for which she earned two Golden Globe nominations.

The New York native later headlined the satire *Lipstick Jungle *(2008–2009) and booked guest arcs on *Law & Order: SVU *(2017–2018), *The Middle *(2010–2018), *Jane the Virgin *(2018–2019), and the Canadian series *When Calls the Heart *(2016–present).

Shields has been married to film producer Chris Hency since 2001. They have two daughters.

*Hannah Montana* is available to stream on Disney+. The *Hannah Montana 20th Anniversary Special* premiered on the platform on March 24.

- Children’s Shows

Original Article on Source

Source: “EW Children’s”