Hannah Montana 20th Anniversary Special: Best and Worst Moments

Twenty years ago, Hannah Montana changed Disney Channel forever — and introduced the world to a 13-year-old Miley Cyrus. Now, Cyrus is celebrating the milestone with an hour-long Disney+ special that's equal parts nostalgia trip, candid confessional and live performance. Hosted by Alex Cooper of the Call Her Daddy podcast, the Hannah-versary — as Miley calls it — brings back the blonde hair, the sequins and the songs that defined a generation.

But how did it all land? Here's a breakdown of the highs and lows.

Best: Hannah's First Performance in 15 Years

There was never any doubt about how the special would open. "Best of Both Worlds" kicks things off with Hannah Montana back onstage in full glory — classic choreography, flowing blonde hair and a sequined outfit that manages to feel both familiar and grown up. Cyrus's vocals have never sounded better, and the crowd's reaction makes clear the song hasn't lost a single bit of its power.

The special's second performance is equally well-chosen. Cyrus opens with "This Is The Life," the very first song she ever performed as Hannah, before moving into "The Climb," the chart-topping ballad that marked the beginning of a new era for the show. It's a two-song set that perfectly bookends Hannah Montana's legacy, and Cyrus delivers both with genuine emotion.

Worst: Only Three Songs

Here's the problem with those performances: there aren't enough of them. Three songs for a 20th anniversary special feels like a significant missed opportunity. "I Got Nerve," "Ordinary Girl" and "Nobody's Perfect" are nowhere to be found. Neither are the Jonas Brothers, who are very much back in the Disney ecosystem and would have been the obvious choice to join Cyrus onstage for "We Got the Party." The performances that do make the cut are genuinely great. There just aren't enough of them.

Best: The Hannah Montana Details

Recreating the Stewart house set. Dyeing Miley's hair Hannah-blonde. Bringing back the show's iconic transition music — that "Ooh-whoa-ooh-whoa-yeaaaah" interstitial that instantly transports any millennial back to 2006. The special clearly had a team of people who cared deeply about getting the nostalgic details right, and it shows. Cyrus also recreates the season three goodbye wave that has since become a full-blown meme, and pulls off the "Hoedown Throwdown" from memory. Because once you've popped it, locked it and polka-dotted it, you never forget.

Worst: Where Was the Cast Reunion?

The special's biggest absence isn't a song — it's the cast. Jason Earles, Moisés Arias and Mitchel Musso are nowhere to be seen. Emily Osment, who played Lily Truscott across all four seasons, was reportedly unavailable due to filming commitments, and her absence is felt throughout. Hannah Montana also had a deep bench of memorable guest stars — Corbin Bleu, Jesse McCartney, Cody Linley — none of whom appear.

Instead, the special's marquee celebrity cameo goes to Chappell Roan, who stops by to offer her appreciation for Cyrus's legacy. It's a sweet moment, but it raises an obvious question: how did a current pop star get the call instead of the people who actually made the show?

Best: Miley Dishes on Her Disney Romances

This is where the special really delivers. Cyrus confirmed long-running rumors that she once dated Dylan Sprouse, calling him her boyfriend and adding that their father would take them out for sushi. "It was a two-for-one," she joked. "Like, bring the brother."

The Nick Jonas revelation is equally entertaining. Cyrus explained that the Jonas Brothers joining the Best of Both Worlds tour wasn't purely a business decision — it was her idea, specifically because Jonas was her boyfriend at the time and she didn't want to go on the road without him. "So I'd be like, 'Okay I'll go on tour if my boyfriend can come,'" she said, "and they were like, 'Cute! Have your boyfriend open for the show.'" It is, as Cyrus herself might say, a power move.

Best: Miley on the Disney Golden Era

Cyrus opens up about what it was like to come of age during Disney Channel's peak era alongside stars who were becoming household names in real time. She recalls that Zac Efron and Vanessa Hudgens were the "coolest kids ever" and that she became fast friends with them. "They loved me, because I was mature for my age," she said. She also admitted that her feelings about Efron have evolved with time, noting that her current appreciation is less about High School Musical Zac and more about the current version.

Best: Miley and Selena Gomez Revisit Their Rivalry

One of the most anticipated reunion moments involves Selena Gomez, Cyrus's former Disney Channel contemporary — and, at various points, her rival. The two address the old tension with humor and warmth, offering the kind of candid acknowledgment that fan communities have been waiting years to see. It's one of the special's more genuinely surprising and satisfying moments.

Worst: The Taylor Swift Tease That Goes Nowhere

Cyrus builds up a story about Taylor Swift's appearance in Hannah Montana: The Movie with the energy of someone about to drop major revelations. What follows is considerably more low-key — a story about how Swift authentically fit the barn setting for her scene and the acknowledgment that Swift wrote "You'll Always Find Your Way Back Home," the song that closed the film. "Credit where credit's due," Cyrus said. "She ate with that one." It's a fine story. It's just not the tea that was promised.

Best: Miley's Emotional Ode to Hannah

The special's most genuine moment comes when Cyrus takes a few minutes after performing "The Climb" to explain what Hannah Montana actually means to her now. She describes how she used to think of Hannah as a separate character — something apart from herself — and how this special has helped her integrate the two.

"What I'm loving about this special is that it's my merging of Hannah and Miley together," she told the crowd.

The special closes with Cyrus debuting a new ballad called "Younger Now," performed against a backdrop of childhood footage and show clips. It's the clearest statement of everything the Hannah-versary is trying to say, and it lands.

Best/Worst: The Credits Clips Show What Could Have Been

The special ends with a collection of candid behind-the-scenes snippets that, ironically, are some of the most fun content in the entire hour. Noah Cyrus appears to present her sister with a cake and share her own Hannah Montana memories — including the fact that she played various small roles across multiple episodes. Billy Ray Cyrus considers trying on the wig. Miley goes through a rack of clothes sorting outfits into "Hannah" and "Miley" categories. These moments are warm, funny and completely unscripted-feeling. It's hard not to wish the special had leaned into this kind of footage a little more and a little earlier.

Curious for more stories that keep you informed and entertained? From the latest headlines to everyday insights, YourLifeBuzz has more to explore. Dive into what’s next.