Dark Secrets The Cast Of Hannah Montana Tried To Hide

"Hannah Montana" may have inspired millions of Disney fans to rock a blonde wig and learn the "Hoedown Throwdown," but the series has a more complicated history than some fans may realize. When a teenage Miley Cyrus auditioned for a part in the series, she had no idea it would be the catalyst for her music career. She probably didn't envision her future self swinging naked from wrecking balls either, but who can blame her?  

While the series was an instant hit, filming the show was anything but seamless. Grueling working hours and rocky interpersonal relationships were just some of the known obstacles involving the show. Many Disney stars went from boasting enormous careers to tarnishing their reputations. From scandalized photos to run-ins with the law, some "Hannah Montana" stars went on to lead lives far different from the innocent teenagers they once played. 

They say that some truths are stranger than fiction, and in the case of "Hannah Montana," some truths are darker too. We're breaking down dark secrets the cast of Hannah Montana tried to hide.

It's hard to imagine that Jackson Rod Stewart on "Hannah Montana" was played by someone a decade older than what was portrayed. Jason Earles took on the role of Jackson Rod Stewart in the series, playing the geeky older brother of Miley Stewart (played by Miley Cyrus). His infectious charm and penchant for getting involved in his sister's messes made him easy to love, especially when he was tongue-tied dating ba ba ba bikini models (that's a Hannah Montana reference for all you none-fanatics). 

But while he and Cyrus played siblings close in age on the show, they were far from close in age in real life. Earles and Cyrus are 15 years apart in age, making for some pretty good acting on their parts if you ask us. Especially when you rewind all the times Jackson was giving his on-screen sister a ride and meddling in her relationship problems throughout the series. 

Earles went on to star in his own Disney XD show "Kickin' It" shortly after "Hannah Montana" wrapped. Years after the series ended, Earles admitted he looks back with fond memories. "If Disney was like, 'Hey, let's do a brand new show, let's do four more years of this' or 'Hey, we're going to do a special six-episode 'Hannah Montana' reunion,' I would do any of that stuff because that place is like family to me," he said on the "Brown and Scoop" radio show (per Teen Vogue).

Miley Cyrus' sparkling Disney reputation didn't exactly follow her when the curtain closed on "Hannah Montana." Once the wig was off for good, Cyrus emerged as the rebellious, boundary-breaking pop star we know her as today. Billy Ray didn't see that coming when he signed on to play his daughter's on-screen dad in "Hannah Montana," however, and it broke his achy breaky heart.  

At the height of "Hannah Montana" fame, Billy Ray's own family was in shambles. "The damn show destroyed my family," he revealed in an interview with GQ. He went on to add that he lost control of his parenting, claiming that the industry had distanced himself from his daughter. "Season four, it was a disaster," he continued. "I was going to work every single day knowing that my family had fallen apart, but yet I had to sit in front of that camera. I look back and I go, How did I ever make it through that? I must be a better actor than I thought."

In the midst of filming "Hannah Montana," Billy Ray filed for divorce from his wife Tish in 2010. Though they eventually called it off, Tish later filed for divorce in 2013. Around the same time, Cyrus accused her father of cheating on Tish with his Broadway co-star Dylis Croman when she shaded him publicly on X, the platform formerly known as Twitter. Billy Ray remained silent over the accusations and he and Tish got back together again that same year until they divorced for good in 2022. 

After Billy Ray and Tish Cyrus officially divorced in 2022 — for good this time — and the "Achy Breaky Heart" found love again shortly after. The country singer started dating Australian singer Firerose and the pair later got engaged. Despite their nearly three decades of age difference, Billy Ray says he found his soul mate. Coincidentally, the "Hannah Montana" actor met her over a decade ago while filming the hit Disney series.

The singer told People that he met his future fiancée while walking his dog during filming takes for "Hannah Montana" and was taken aback immediately. "Firerose came out of the front door. There was almost a moment of, I don't know, recognition. I was like, 'This girl's a star," he said of meeting her on the set of the show 12 years ago. While Billy Ray had no idea who Firerose was, the Australian artist had grown up listening to Billy Ray. "I've known his music since forever," she admitted.

Billy Ray explained that he attempted to share his contacts with Firerose and they ended up bonding. "And so, off me and her and Tex went back to the studio and I think she met a lot of the cast and met the producers, writers. And, in some ways, well, in a lot of ways, we became friends," he admitted. Years later, after several divorce filings and an official separation from his ex-wife Tish, the pair reconnected romantically in 2022. 

Despite being the face of the "Hannah Montana" franchise, Miley Cyrus said she was the least-paid actor on the show. With big dreams of making a career for herself, Cyrus admitted in an Elle interview that paychecks were the least of her concerns during her early days. "I just wanted to be on TV. I mean, at one point—they'll probably kill me for saying it—I was probably the least paid person on my [Hannah Montana] cast because I didn't know any better. I was just like, 'I can be on Disney! Yeah, I want to do it!'" she explained. 

Cyrus isn't the only one who felt underpaid in the series. Her father Billy Ray claimed he was receiving next to nothing compared to what Disney was racking in with "Hannah Montana. "I knew I was working for peanuts. I'm not the smartest man in the world, but I know the difference. I went from $12,000 a week to, after four years and the millions that they make, $15,000 a week. Hell, yeah," the country singer revealed in an interview with GQ. 

With time comes wisdom, and Miley learned that the hard way. The "Wrecking Ball" singer revealed that she and her family eventually learned the importance of trademarks and the tricky business deals of Hollywood. "Like, 'Yeah, you can use my name on your show, sure!' Cyrus joked. "My mom started understanding how many people take advantage of a child, so she hired smart people to protect me in that way."

Miley Cyrus' blonde wig and pop star persona covered up a lot more realness than fans realize. While Miley Cyrus' character was disguised under the guise of "Hannah Montana," so were her real-life personal struggles. In an interview with Marie Claire, the "Miss You So Much" singer opened up about the toll of being a child star.

For Cyrus, a normal childhood was overshadowed by the enormous pressure of upholding the face of a Disney franchise. "From the time I was 11, it was, 'You're a pop star! That means you have to be blonde, and you have to have long hair, and you have to put on some glittery tight thing.' Meanwhile, I'm this fragile little girl playing a 16-year-old in a wig and a ton of makeup. It was like 'Toddlers & Tiaras.' I had f**king flippers," she admitted.

The singer admitted she was forced to work grueling 12-hour days, even after getting her first period on set. She recalled telling her mom, "'You're going to have to put the tampon in. I have to be on set.'" Cyrus admitted that the pressure to maintain the look of Hannah Montana caused her to question her own appearance. "I was made to look like someone that I wasn't, which probably caused some body dysmorphia because I had been made pretty every day for so long, and then when I wasn't on that show, it was like, Who the f**k am I?" she explained.

Miley Cyrus has had a number of controversial media moments over the years. As she grew older, she became less of the blonde pop star Disney introduced her as and more of the twerking, foam-finger-wagging, unapologetic artist we know her as today. Fans got a glimpse of a more mature Cyrus when she posed topless for a Vanity Fair spread in 2008. The spread, dubbed "Miley Knows Best" featured the artist in red lipstick wearing nothing but a silk robe as she covered herself with her bare back to the camera. 

The photos prompted major media backlash and led to the star issuing an apology at the time admitting she was embarrassed and she "never intended for any of this to happen and I apologize to my fans who I care so deeply about." Disney released their own statement at the time saying: "Unfortunately, as the article suggests, a situation was created to deliberately manipulate a 15-year-old in order to sell magazines."

It wasn't the only time Disney had a response to Cyrus' antics. The singer caused controversy during the 2009 VMAs when she performed "Party In The U.S.A." holding onto a metal pole attached to an ice-cream cart prop. Many viewers criticized Cyrus for what they believed was the "Hannah Montana" star dancing on a stripper pole. Disney Network responded to the criticism at the time saying they "won't be commenting on that performance," adding that content aired on their network is "consistent with what our brand values are" (via Billboard).

Miley Cyrus and Emily Osment played the best of friends on "Hannah Montana" for years, but off-screen a far different reality was playing out. In Cyrus' 2008 autobiography "Miles To Go" (per Elite Daily) the actor admitted that she and her co-star were constantly fighting on the set of the show, with their parents even separating them times. "Emily and I tried to be friends, we really did, but it always ended in a fight," she wrote in her book. "Our characters got along so well, why couldn't we act the same in real life?"

A year prior, the "Last Song" actor described their relationship a bit differently. "When we first met we had an instant friendship and now we're more like sisters. We love each other like sisters. We fight like sisters. It's always like that," she told Seventeen.

Despite their hiccups, Cyrus and Osment seem to be on good terms. In 2013, the "Love Is All You Need?" star tweeted at her former co-star, writing: "need you back in my life, bro." The "Adore You" singer responded back, "Miss u. Hit me on DM." Their long-anticipated reunion came true when Osment joined Cyrus in 2020 on her Instagram Live series "Bright Minded."  The two reminisced on their Disney days, with Cyrus joking about the intense working schedule the two endured as child stars. "I remember that that was kind of our life for eight years — every day just longer than we were warned," she said.

"Hannah Montana" star Mitchell Musso made headlines in 2023 after the actor was arrested for public intoxication and theft. According to a police report from the Rockwall County Police Department, Musso entered the SpringHill Suites Dallas Rockwall, grabbed a bag of chips, and started eating them. The star was asked to pay and became "verbally abusive and left without rendering payment." After displaying signs of intoxication, Musso, who played Oliver Oken on the Disney series, spent one night in jail before posting a $ 1,000 bond.

After the controversy, the Disney star told Entertainment Weekly: "I was absolutely not drunk or drinking, and there was 100% no theft. It's unfortunate, it's a misunderstanding." Musso explained that he entered the hotel shirtless after coming off a nearby boat. Intending to restock the snack supply, the employee snatched the bag of chips out of his hand. "I didn't know it was illegal not to wear shirts these days," he said, adding that the employee "told me to 'get the f— out,' were the words he used. And that kind of set me off. And he said, 'I'm gonna call the police' and I said go for it."

As to his alleged "verbally abusive" behavior, Musso admitted: "I was the one who was being verbally abused and also harassed. Someone ripping something out of your hand is not the most polite manners to have in this situation." The manager at Springhill Suites responded in a comment that "He can say whatever he wants to say. That's his story, that's fine."

It's not exactly the best look to get caught in bed shirtless with a minor, but these days anything goes in Hollywood. Moisés Arias landed himself in the tabloids for doing exactly that when a controversial photo surfaced of him in bed with singer Willow Smith. In the black-and-white photo, Arias is seen laughing shirtless on the bed while Smith lies beside him. Though the photo is seemingly harmless, it sparked major backlash online. Viewers dubbed it scandalous given that Smith was just 13 at the time and Arias was 20.

Smith's mother Jada Pinkett Smith responded to the controversy, telling TMZ: "Here's the deal: There was nothing sexual about that picture or that situation, adding, "You guys are projecting your trash onto it, and you're acting like covert pedophiles, and that's not cool."

It doesn't look like the "Wait a Minute!" singer had much to worry about in terms of punishment. Will Smith told Metro (via E! News) that he and Jada Pinkett Smith "don't do punishment," adding that "The way that we deal with our kids is, they are responsible for their lives. Our concept is, as young as possible, give them as much control over their lives as possible and the concept of punishment, our experience has been—it has a little too much of a negative quality." As per Arias, the former "Hannah Montana" star didn't respond to comments over the polarizing images.