An Extremely Realistic Headcanon of What Hannah Montana Has Been Up to for the Past 20 Years

For the past few weeks, Miley Cyrus has been teasing something big for the 20th anniversary of Hannah Montana in 2026, but so far, we’re in the dark. A new album? A world tour? An HBO limited series? Who knows. But one thing’s for sure: Hannah Montana is being resurrected.

When we last saw Miley Ray Stewart/Hannah Montana in 2011, she did something crazy: She dramatically yanked off her iconic yellow wig on the Tonight Show with Jay Leno (jump scare) and revealed her true identity to the world, shocking nine-year-olds everywhere. Miley/Hannah was in the throes of a full-blown identity crisis. And we related, ya know, as nine-year-olds.

Looking back, I forgot just how wild this season was: After getting rejected from Stanford and passing on a Spielberg movie deal, Miley chooses to stay roommates with her lifelong bestie Lily, walking away from stardom for good (or, for now).

No one saw the public offing of Hannah Montana coming. But what happened after that? Please indulge me in this imagined life story of a one-in-a-million pop star as she grows up in the same nightmare hellscape the rest of us did.

2011–2012: The College Era (Short-Lived)

Miley Ray manages to weasel her way into Stanford with the help of Robby Ray and some light bribery. In my opinion, she majors in something like “undecided,” but it quickly becomes clear that college isn’t her thing. She grows distant from Lily after they fail to fall into the same crowd post-high school. Plus, she cannot handle living more than 20 minutes from the nearest beach. She drops out. But not before partying it up a little and getting really into Snapchat and American Apparel. Next stop: Miley’s Post-Dropout Activist Era.

2013-2016: Activist Era

Robby Ray is mad. If Miley doesn’t “do something,” he threatens to cut off the Hannah Montana trust fund. So, she becomes an activist<3 She dances in Pride parades; she posts selfies in #ImWithHer merch; she begins seeing a therapist 2-3 times a week to talk through her dual personalities. When Hillary loses, it hits hard. She announces that she is going on a social media break via several Instagram posts. But then goes on Vine.

Sometimes, she still feels Hannah’s presence gnawing at her from the inside. She’s unemployed and struggling. So, she hires an unpaid assistant to help resell her old Hannah wardrobe on Depop and The RealReal. That doesn’t pay the bills. So, she jumps to the next logical move: cash grabs.

2017-2019: The Shameless Cash Grabs

At some point in 2017, she was approached by Sugar Bear Hair to push the infamous gummies on Instagram for a modest sum. I mean, let’s be real, her hair is like, her whole brand. She accepts. Then comes the signature hair care line. Then the wig line. Then the failed makeup brand. She’s in her early twenties, and she’s experiencing all the highs and lows that come with being a former child star turned businesswoman. Everybody makes mistakes, and everybody has those days.

Next, she has a ghost writer write her memoir, The Other Side of Me, in which she TELLS ALL about life as a pop star, the PTSD she carries from leading the double life, and a torrid affair with the aforementioned therapist. Obviously, it becomes a #1 New York Times Bestseller, and it even gets blurbed by Malala.