The Ultimate Disney Channel Crossover: 5 Surprising Facts About AJ Michalka’s Friendship With Miley Cyrus And The Role That Got Away

The connection between AJ Michalka and Miley Cyrus is a fascinating deep dive into the intertwined world of 2000s Disney Channel royalty, revealing a history far more complex than just sharing a network. While both artists have successfully navigated the transition from teen idol to respected adult musician and actress, their professional paths nearly merged in a way that would have fundamentally changed pop culture history. The two stars, who are close in age, shared a camaraderie built on the pressures of early fame, culminating in shared stages and memorable backstage moments that AJ Michalka has recently reflected on, offering a fresh, nostalgic look at their "down-to-earth" friendship during a pivotal era. The latest updates, as of December 12, 2025, center on Michalka's candid recollections of their time together, especially the major "what if" moment involving the role of *Hannah Montana*.

The shared history of Amanda Joy "AJ" Michalka and Miley Ray Cyrus is a significant piece of pop culture lore, primarily stemming from their time on the Disney Channel. Beyond their respective shows, *Phil of the Future* for AJ and *Hannah Montana* for Miley, their connection was cemented when AJ, alongside her sister Aly Michalka, as the musical duo Aly & AJ, served as the opening act for the monumental *Hannah Montana/Miley Cyrus: Best of Both Worlds Tour*. This period fostered a genuine friendship, with AJ recently sharing "adorable" core memories of their time together, highlighting the genuine connection between two young women experiencing unprecedented fame. The most compelling revelation, however, involves the casting of the iconic Disney series, a story that continues to fascinate fans and media alike.

AJ Michalka & Miley Cyrus: A Dual Biography Profile

To fully appreciate the intersection of their careers, it's essential to understand the parallel yet distinct paths these two influential artists took.

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Amanda Joy "AJ" Michalka

• Full Name: Amanda Joy Michalka
• Born: April 10, 1991, in Torrance, California, U.S.
• Primary Roles: Actress, singer-songwriter, musician.
• Career Highlights (Acting): Role as Keely Teslow on the Disney Channel series *Phil of the Future* (2004–2006); Lainey Lewis on the ABC sitcom *The Goldbergs* (2013–2023) and its spin-off *Schooled*; Voice of Stevonnie in the animated series *Steven Universe*.
• Career Highlights (Music): One half of the musical duo Aly & AJ, alongside her older sister Alyson "Aly" Michalka. Known for hits like "Potential Breakup Song" (2007) and "Rush" (2005). The duo successfully re-emerged in the late 2010s with a more mature, synth-pop sound.
• Other Entities: Hollywood Records, *Cow Belles*, *The Lovely Bones*.

Miley Ray Cyrus

• Full Name: Destiny Hope Cyrus (Legally changed to Miley Ray Cyrus)
• Born: November 23, 1992, in Franklin, Tennessee, U.S.
• Primary Roles: Singer, songwriter, actress.
• Career Highlights (Acting): Role as Miley Stewart/Hannah Montana on the Disney Channel series *Hannah Montana* (2006–2011); Films like *The Last Song* and *Guardians of the Galaxy Vol. 2*.
• Career Highlights (Music): Grammy-winning global superstar known for her constantly evolving artistry and image. Major hit songs include "Wrecking Ball," "Party in the U.S.A.," "The Climb," and the Grammy-winning "Flowers." She has released multiple platinum-selling albums, starting with *Meet Miley Cyrus* and *Breakout*.
• Other Entities: Billy Ray Cyrus (father), Tish Cyrus (mother), Disney Music Group, RCA Records, Liam Hemsworth.

The Shocking 'What If' Story: How Aly & AJ Nearly Became Hannah Montana

The most compelling and recently discussed element of the AJ Michalka and Miley Cyrus connection revolves around the casting of *Hannah Montana*. This revelation, often brought up in recent interviews with Aly & AJ, provides a significant pivot point in pop culture history, underscoring how close the Michalka sisters were to starring in the series that launched Miley Cyrus into global superstardom.

1. The Original Offer for the Title Role

In a story that has gained significant traction in recent years, Aly Michalka revealed that she was originally offered the lead role of *Hannah Montana*. The Disney Channel, recognizing her talent from *Phil of the Future*, approached Aly to star as the titular character. Aly, however, ultimately turned down the offer. She and her sister, AJ, felt that committing to a long-running series would prevent them from fully focusing on their burgeoning music career as Aly & AJ, which was their primary passion at the time. This decision opened the door for Miley Cyrus, who was initially auditioning for the role of Lilly Truscott, to land the lead role.

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2. AJ Was Offered Lilly Truscott

The casting overlap didn't stop with Aly. AJ Michalka confirmed that she was offered the role of Lilly Truscott, the best friend of Hannah Montana (Miley Stewart). This role eventually went to actress Emily Osment, who became a beloved figure on the show. Had both Michalka sisters accepted their respective roles, the dynamic of the show and the entire trajectory of the Michalka's music career would have been drastically different. The sisters have expressed no regret, stating they believe the role was "meant for Miley Cyrus to take."

3. The Tour That Cemented Their Friendship

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Despite turning down the acting roles, the Michalka sisters’ path soon crossed with Miley's in a massive way. Aly & AJ were selected as the opening act for the highly anticipated *Hannah Montana/Miley Cyrus: Best of Both Worlds Tour* in 2007–2008. This tour was a cultural phenomenon, selling out arenas across the United States and generating over $54 million in revenue.

The experience of touring together created a bond. AJ Michalka has spoken fondly of the time, recalling that touring allowed them to be "giddy and young" together, sharing the experience of massive fame and demanding schedules. This shared experience solidified a friendship that transcended the network rivalry that often defined the era.

AJ Michalka’s Fondest Memories of Miley Cyrus: "Down-To-Earth"

In recent interviews, AJ Michalka has been highly complimentary of Miley Cyrus, painting a picture of a genuine, grounded person behind the Disney Channel persona. These recollections are what keep the "AJ Michalka Miley Cyrus" search term relevant today, as fans are always curious about the true nature of celebrity relationships from that golden era.

4. Recalling "Core Memories" and Genuineness

AJ recently shared that she has "core memories" of her time with Miley, emphasizing that the singer was "down-to-earth" and "adorable." She described the backstage environment during the *Best of Both Worlds Tour* as a place of genuine connection, where they would interview each other and share the excitement of their new premieres. This sentiment is a refreshing counter-narrative to the often-rumored rivalries among Disney stars, highlighting a period of authentic camaraderie.

5. The Jonas Brothers Connection and Shared History

Another entity that ties the two stars together is the Jonas Brothers. Both Aly & AJ and Miley Cyrus were prominent figures in the same social and professional circles as the Jonas Brothers, who were also Disney Channel staples at the time. Aly & AJ famously had a close relationship with Miley and were reportedly among the first to hear the truth about the highly publicized breakup between Miley Cyrus and Nick Jonas. This shared history of navigating early celebrity relationships and the intense scrutiny that came with them is another layer to the complex tapestry of their connection.

The shared legacy of AJ Michalka and Miley Cyrus is a powerful reminder of a specific moment in pop culture. While their careers have diverged—Miley becoming a global pop icon and AJ focusing on her successful dual career in acting (*The Goldbergs*, *Schooled*) and music with Aly & AJ—the "what if" of the *Hannah Montana* casting remains the most fascinating piece of their story. AJ and Aly's decision, which allowed them to pursue their musical passion, ultimately led to the creation of the Aly & AJ discography, while simultaneously paving the way for the phenomenon of Miley Cyrus's career. Their mutual respect and AJ's recent nostalgic reflections confirm that their relationship, forged in the crucible of Disney stardom, was one of mutual support and genuine friendship.