20 years later, the Disney sitcom remains a pop culture phenomenon. For those of us who grew up watching the show, its two-decade anniversary serves as a nostalgic trip — but revisiting the series is a double-edged sword. On one hand, Hannah Montana is as iconic as ever, but on the other hand, the show’s magic doesn’t quite hit the same.
Hannah Montana was, in many ways, a product of its time. Sure, it wasn’t a perfect series by any means, given how critics panned it because of its problematic storylines. But even while I peeled back the layers during my latest rewatch, one thing remains for certain: Hannah Montana’s legacy can’t truly be taken away.
Some Jokes From Hannah Montana Haven’t Aged Well
Hannah Montana had some pretty great jokes that are still funny. From iconic pick-up lines delivered with absolute precision to situational humor, the series was consistently hilarious. However, there are instances when the show went too far with its jokes. Seeing as Hannah Montana was a kids’ show, some of its humor wasn’t age-appropriate.
Granted, the kids watching the show probably wouldn’t understand the double entendres, like the poorly aged line, “She wants to take a ride on the Ollie Trolley,” but including them in something meant for kids was a questionable decision. It’s not just the sexual jokes that were concerning; Hannah Montana often crossed the line with its sexist and body-shaming zingers.
Thor, one of the guest characters in the sitcom, was subjected to fatphobic jokes, and what’s worse is that Hannah Montana didn’t add depth to him. Instead, Thor was portrayed as a stereotypical “fat person.” That kind of humor was common in comedy TV shows during the time Hannah Montana was airing, but I can’t help but wince when I rewatch those moments.
Miley Wasn’t Always A Good Friend
One reason Hannah Montana was such a great show was its emphasis on Miley, Lilly, and Oliver’s friendship. The trio was a perfect match. Their personalities gelled, and their different types of humor elevated the series. However, that doesn’t mean that Miley was always a great friend, nor were her friends always good to her.
Miley constantly lied to Lilly and Oliver. First, it was the Hannah Montana secret she was keeping from them, then the lies became about other things. For instance, when Lola’s behavior embarrassed Hannah, Miley kept the truth from her friend instead of just being upfront about how uncomfortable it made her feel. When Miley’s boyfriend cheated on her, she lashed out at messengers, instead of the person who hurt her.
Lying, taking her friends for granted, and keeping secrets were just another Tuesday on Hannah Montana because that’s how the show was set up. Miley created a problem, and it was miraculously solved at the end of each episode. Some argue that Miley, Lilly, and Oliver were just teenagers, so their behavior was typical for that age.
While that is true, it doesn’t negate the fact that Miley’s selfish behavior, while somewhat typical for a teenager, takes away some of Hannah Montana’s glitter and magic. But it’s worth noting that Miley wasn’t meant to be a terrible person. She was just a flawed teen growing up and learning lessons, but her continuously repeating the same mistakes grew tedious.
Jackson Was Treated Like A Joke
Sitcoms usually have a character who gets a lot of spotlight, but not so much that they outshine the primary protagonist. In Hannah Montana, it was Miley’s brother, Jackson. The older Stewart sibling was always less than his superstar sister. He was portrayed as incompetent and bad at everything: school, jobs, and decision-making. Even when he tried to do better, the show couldn’t help but try to extract a joke out of it.
Watching Hannah Montana now, Jackson’s mistakes feel less goofy and more like that’s who he was as a character. His romantic rejections became a running gag, and he was often belittled, ignored, or put in embarrassing situations, just for laughs. Jackson deserved better than to be portrayed as a one-dimensional character who never did anything right.
Robby’s Parenting Was Questionable
20 years after Hannah Montana’s debut, the biggest issue I have with the show is Robby’s parenting style. He allowed his teenage daughter to live a secret life, which seemed like a lack of protection and boundaries. Sure, he might have done it so she could live a “normal life” free of the burden that comes with being a celebrity, but Miley’s situation was anything but ordinary.
What’s more, is that she lied to the whole world and her fans for years. Although Robby clearly loved his two children, it can’t be ignored that Jackson more often than not took the backseat to Miley’s needs. This seemingly didn’t bother Robby until his mother pointed out the fact that Jackson was left out far too many times.
Rico Was A Toxic Character
Rico Suave was written as a character who was meant to be annoying, and that was a bit funny, to some extent. However, it’s pretty clear that a lot of his behavior crosses from “mischievous kid” into straight-up toxic territory. As Jackson’s boss, he often played humiliating pranks on his employee. He was manipulative and a bully who had no qualms about using his wealth to control others.
Rico is a poster child for toxic masculinity. He often objectified women and sexualized them to a point where it was less of a running joke and more of a need for an intervention. Unfortunately, he was never punished for his crimes. Throughout Hannah Montana‘s entire run, Rico did terrible things and got away with them.
Hannah Montana’s Double Life Plot Doesn’t Make Sense
As a child, I thought it was cool that no one figured out that Hannah Montana was Miley Stewart. But looking back, it was so obvious that she was the famous pop star, especially to the people who knew her well, like Oliver and Lilly. Her blonde wig disguise and Southern twang were simply not enough to fool her close circle of friends.
Add in the fact that her father was famous in his own right and had a poor disguise as well, and it made no sense that no one put it together. However, I can’t help but see how unfair the whole charade was and how it would eventually lead to burnout. Miley had to lie to people she cared about on several occasions, and she also had to balance her normal life with the strains that come with fame.
Despite Its Flaws, Hannah Montana’s Songs Are Still Great
Disney excels when it comes to music. So many songs featured in the production company’s movies and TV features have become classics. Hannah Montana’s music was simply the heartbeat of the show. Every time I hear “The Best of Both Worlds,” I’m immediately taken back to that era, and watching the anniversary special reminded me of how spectacular the show was.
While many popular 2000s songs have lost their allure, Hannah Montana’s are still hits. The series might not have aged well in some respects, but songs like “If We Were a Movie,” Nobody’s Perfect,” and “Wherever I Go” are proof that Hannah Montana has enduring appeal.