One of the longest running Disney Channel series, Hannah Montana ruled the network for five years. The 2006 debut of the series catapulted Miley Cyrus into star status. With the popularity of the series came the big screen feature Hannah Montana: The Movie and a slew of Disney Channel original series and movies for the supporting cast members.
After 101 episodes, fans had to say goodbye to the friends they watched grow up on screen. With the show focused on Miley’s double life as pop star Hannah Montana, the title character had friends in both worlds of her life. Miley made friends at school while Hannah hobnobbed with celebrities. The result was an interesting mix of meaningful relationships and tabloid frenemies for the series.
Best: Lilly And Joanie
Introduced early in the series, but not fleshed out until much later, Joanie was a long time rival of Lilly’s. The two competed in athletics and didn’t get along well off the field. When Joanie started dating Lilly’s best friend Oliver, it seemed they would become permanent enemies, but that changed.
Thanks to an intervention from Miley, they found they actually had a lot in common. The experience gave Lilly a friend outside of the Hannah Montana circle, and meant that she had someone who shared her interests.
Worst: Hannah And Traci
Traci didn’t make a ton of appearances in the series, but when she did, fans knew they were in for a Hannah-focused episode. Traci only knew the popstar alter ego of Miley Stewart, not the girl underneath the wig.
When Hannah and Traci hung out, it was all about parties and status. Traci didn’t seem to have any interests outside of appearing rich and famous. It’s hard to understand why Miley-as-Hannah would want to hang out with her since she hated the same traits in Amber and Ashley at school. Traci also pranked Hannah by pretending to be engaged to her ex boyfriend, which seemed like a pretty horrible thing for a friend to do.
Best: Oliver And Jackson
Oliver didn’t have a lot of friends outside of Lilly and Miley. Though there were references to him hanging out with “the guys,” anyone else was rarely seen. With Jackson’s life so wrapped up in the Hannah Montana secret, the same was true for him after the first season.
It was good that they were able to bond. There were plenty of times in the series in which Lilly or Oliver hung out with Jackson without his little sister there, but Oliver had that honor more than Lilly. Neither Jackson nor Oliver were the smartest characters on the show, but they were both inventive and always ready to have a good time, so the audience never saw them have an argument.
Worst: Amber And Ashley
Amber and Ashley were the equivalent of queen bees in Hannah Montana. Every year, Lilly and Miley found themselves at odds with the duo, but the two friends were even at odds with one another.
Amber and Ashley both loved the spotlight, and they didn’t like to share it. Though they seemed joined at the hip through the series, they were both perfectly happy to kick each other to the curb if it meant a musician paid attention to them, or if it meant their classmates were impressed with their new car. Not being able to share with a best friend seems like it would crack the foundation of a friendship fairly quickly.
Best: Miley And Oliver
Despite Miley not being into skateboards, or surfing, or beef jerky, she somehow formed a friendship with Oliver. The two were nearly as inseparable as she and Lilly.
Throughout the series, Miley seemed very conscious of the fact that Oliver and Lilly were friends first, and went out of her way to make sure she didn’t ruin her friendship with either of them - or theirs with each other. When Oliver had a crush on Hannah Montana, Miley tried to find a way to let him down easy, then resorted to trying to make Hannah absolutely unappealing to him. The experience could have made a mess of things, but instead, Oliver accepted the fact that Miley was Hannah and never told her secret. It didn’t even make things awkward that he used to have a crush on her alter ego!
Worst: Jackson And Rico
Though Rico was much younger than most of the main Hannah Montana characters, he became a fixture on the series very quickly as Jackson’s boss. Yes, the pint sized rich kid was the boss for a concession stand on the beach.
Rico thought of Jackson as his friend, though he never treated him that way. Instead, Rico withheld earnings from him, taunted him, and repeatedly tried to get him in trouble. For his part, Jackson was rarely able to act like the mature one in the situation, taunting Rico and defying him on a regular basis.
Best: Lilly And Oliver
Before the Stewart family moved out to California and began Miley’s career as Hannah Montana, Lilly already had a best friend. She and Oliver had known each other since pre-school.
Lilly and Oliver grew up together, learned to skateboard together, and went through the trials of puberty together. They had a bond that wouldn’t break, even when Miley became a part of their friend group.
Of course, Lilly and Oliver also gradually became something more. Though they both had other relationships in their high school years, by the time they graduated, they had been the longest running couple of the series. They even stayed together while he became a musician on tour and she decided to attend university.
Worst: Hannah And Mikayla
Mikayla was a rival pop star played by Disney Channel alum Selena Gomez in one of her earliest roles for the network. While Hannah and Mikayla always acted like they were friends on camera and in front of reporters, the truth was very different.
Mikayla was jealous of Hannah’s success and went out of her way to sabotage her. Hannah, for her part, secretly despised Mikayla as well. She tried to out Mikayla as mean and spoiled to the press. It didn’t help the situation that Mikayla actually liked Miley when she met her and wanted to befriend her to bond over their mutual dislike of Hannah Montana.
Best: Lilly And Miley
With Oliver gone for long stretches of time, the friendship trio often became a duo. The series also made it clear early on that Miley befriended Lilly first when she moved to California, giving them a more immediate connection than Miley had with Oliver.
Lilly was the first person outside of her family that Miley told about her secret identity as pop star Hannah Montana. It’s no coincidence that Lilly is the only one of her friends who gets to see where she came from in Hannah Montana: The Movie as well. The two were closer than sisters, prompting Miley to put her life as Hannah on hold so she could go to college with her best friend.
Worst: Hannah And Lola
Fans might wonder how Hannah and Lola land as one of the worst friendships on the show when they’re simply the alter egos of Miley and Lilly. They might have been the same people, but they acted very differently toward one another once they donned their respective wigs and costumes.
As Lola, Lilly wasn’t her down to earth self. Instead, she was obsessed with freebies and using her connection to Hannah to meet celebrities, attend movie premieres, and more. Likewise, Hannah wasn’t above leaving Lola behind to get a good opportunity for her career. The personality changes were necessary to differentiate them from their real selves, but they made for a less than stellar friendship when playing their parts.