Top 17 Saddest Disney Channel Moments That Made You Weep

If you grew up in the late ’90s or early 2000s, there’s a huge chance that Disney Channel was an integral part of your upbringing. Whether you were sitting down for a Boy Meet World marathon, or watching a few of your favorite Disney Channel Original Movies — there are certain moments that stuck with you forever.
Although Disney Channel’s programming was mostly lighthearted and kid-friendly, there were a few times Disney got so real. So, here are 17 unforgettable Disney moments that most definitely made you weep:

When Gordo had to go to high school early

Let’s be real, there was no Disney Channel character more pure than Gordo from Lizzie McGuire. He was incredibly sweet, caring, generous, and of course — crazy smart. So smart, in fact, that he gets the opportunity to skip a grade and attend high school early! Unfortunately, Gordo immediately realizes the mistake he has made. He’s incredibly lonely, the high schoolers are jerks, and to top it off? There’s a heartbreaking montage of him walking through the dark hallways while “Everybody Hurts” by R.E.M. plays. It was absurdly cheesy but definitely effective.

When Louis lies to Ren to let her win a game show

In this episode of Even Stevens, we see Louis have a brief (and rare) moment of pure kindness and love for his sister, Ren. Basically, the siblings enter a game show to end their constant bickering. The show, called “Sibling Rivalry,” allows siblings to compete against each other. For the final challenge, each sibling must try to embarrass the other one the most. In Louis’s incriminating video, he caught Ren’s boyfriend cheating on her. Instead of showing it, he lets her win, then tells her about her boyfriend’s indiscretion in private. It’s a heartwarming and classic Disney Channel moment, and boy did it make us cry.

When Miley’s dad lets her go to Florida

In this tearjerker of a Hannah Montana episode, Miley gets into one of the realest arguments with her dad, Robby Ray. When Hannah starts her feud with Mikayla (played by Selena Gomez), she realizes she has to show her who’s the best singer by playing a killer show in Florida. However, when Robby hurts his back and can’t take the plane with her, he refuses to let her go alone. It turns out that it’s because he can’t stand the thought of her growing up. He ends their argument by playing a song he wrote, called “Ready, Set, Don’t Go.” We’re not crying, you are.

When Raven championed body positivity

This was another one of those Disney Channel moments that really hit home for insecure middle-schoolers. In this episode of That’s So Raven, one of Raven’s designs get chosen to appear in a magazine ad. However, when she poses for the photo shoot in her original design, they end up photoshopping someone else’s body underneath her face. At first, she’s obviously upset. But in true Raven fashion, she jumps on the runway during a fashion show wearing the dress, and says “People come in all shapes and sizes, and they’re all beautiful.” Happy tears.

When Gordo helps Lizzie after a breakup

Another scene with Gordo being every tween’s total Disney Channel dream boy. Basically, we all have to sit and watch Gordo suffer while Lizzie pines after Ethan Kraft and then dates Ronnie, the paperboy. And of course, Ronnie AKA “Pudding” (her secret codename for him) was the worst of the worst. They fall for each other pretty quickly, but it was too good to be true — Ronnie chooses another girl over Lizzie.
Gordo to the rescue! Gordo consoles Lizzie, and tells her that “there’s nobody prettier than you, or more fun to be with.” Then, it looks like he’s about to confess his love for her, but shuts up. This scene effectively ripped out and stomped on the hearts of every 12-year-old in America.

When Troy and Gabriella kind of break up

When it comes to dramatic and sad Disney Channel moments, few are as iconic as Troy and Gabriella’s duet on “Gotta Go My Own Way” in High School Musical 2. It starts when Sharpay bans any of the staff members at Lava Springs from performing in the talent show and Gabriella is finally fed up and quits her job. Troy tries to get her to stay, but Gabriella has had enough of his totally selfish attitude and general badness throughout the Summer. So naturally, she starts singing about it. She even gives him back the necklace he gave her. They really made it seem like Gabriella and Troy were done for good. Cue: waterworks.

When we learned about Dorinda’s backstory

Cheetah Girls is one of the most popular movies in Disney Channel history, and with good reason. It’s all about talented girls finding themselves and supporting each other along the way. Plus, each girl comes from a pretty diverse background, which made it really unique and interesting for its time. However, no scene tugged at our heartstrings more than when we learn that Dorinda has been bounced through foster homes throughout her childhood, and currently lives in a housing project without her biological sister.

Pretty much every scene in Tru Confessions

Tru Confessions is one of those Disney Channel movies that makes you think: really? I watched this when I was eight? You most likely spent the entire movie choked-up or full-on ugly crying. The movie follows a boy named Eddie (played by Shia LaBeouf), who was born with autism. His twin sister, Tru, decides to film his life as a documentary for a film contest. Seeing the way that Eddie is treated by his schoolmates, the outside world, and his family was hard to watch then, and it’s still truly heartbreaking.

Mr. Feeny’s closing words

Boy Meets World is quite possibly the most iconic show from the Disney Channel, even though it technically premiered on ABC. We grew up with each character and got to see them deal with real issues. Once reruns began playing on Disney, it was like a whole new generation of us got to see them go from awkward high schoolers to real-life adults. And throughout all of that, no moment was more heartbreaking than Mr. Feeny’s final words: “I love you all. Class dismissed.” *SOB*

When Raven had to deal with racism

Disney Channel got really real once again with this super-memorable episode of That’s So Raven. Although the show rarely dealt with heavy issues, one episode, in particular, decided to cover the topic of race. In “True Colors,” the kids’ parents set the tone by trying to teach them about African-American history. This becomes relevant when Raven learns she wasn’t hired to work at a store because she’s black. For a Disney show, this was pretty uncharted territory, and it really struck a chord with young audiences.

When Alex and Justin share a beautiful sibling moment

Who knew that Disney Channel would absolutely ruin our lives with the Wizards of Waverly Place: The Movie? To summarize, there’s a point in the story where Alex wishes her parents never met and a whole lot of magical drama to go down. Her family members slowly start losing their memories and forgetting their pasts, and it turns out they’ll eventually disappear if Alex doesn’t find a way to reverse the wish. At the end of the movie, Alex needs Justin’s help with solving this whole disaster, but he can’t remember who she is. She breaks down crying and tells him about their relationship to try and recover his memory. She confesses how much she loves him and admires him, and Selena Gomez did an amazing job because there’s no way anyone could watch that scene without sobbing.

When Miranda dealt with body image issues

Granted, this whole plotline was incredibly short-lived, but it definitely made an impact on its teen audience. Although Disney Channel mostly avoided ~serious~ topics, this episode of Lizzie McGuire did its best to talk about body image and eating disorders. When they’re filming a music video for Gordo’s project, Miranda can’t stop obsessing over how “fat” she looks. She nearly passes out from skipping meals, and her friends finally convince her that she’s perfect the way she is. Now, it seems a little trivializing, but for insecure tweens everywhere, it was an incredibly tense and emotional moment.

When Miley saw her mom in a dream

The subject of Miley’s mom rarely came up on Hannah Montana (in typical Disney Channel fashion), so all we really know is that she passed away when Miley was pretty young. One morning, Miley wakes up with laryngitis. In order to save Hannah’s career, she has to undergo surgery. While she’s asleep, Miley’s mom comes to visit her in a vision, to tell her that everything is going to be okay and that she always has the support of her love and family. It’s such a beautiful moment, even the most hardened viewers were brought to tears.

Mr. Feeny’s heartwarming speech to Shawn

Although Mr. Feeny loved to be a tough love kind of guy, we all know that deep down he had a heart of gold. Avid watchers of Boy Meets World will remember the one episode where he made a beautiful speech to Shawn, who was upset about the state of his dysfunctional family. Shawn begins arguing with Cory while trying to defend his family, and it turns into a huge fight. Shawn thinks that he doesn’t need Cory because family is all that matters — to which Mr. Feeny says “Mr. Hunter, you don’t have to be blood to be family.” Goosebumps!

When Kim and Ron finally kissed

Kim and Ron from Kim Possible were a Disney Channel power couple if there ever was one. Kim was the badass, beautiful, crime-fighting redhead, and Ron was her lovable, kind-hearted and completely dorky sidekick. It was obvious that Ron was always in love with Kim, but it wasn’t clear whether they would end up together. Thankfully for Kim Possible fans, they made the whole thing official after the kiss and Junior Prom. It was a beautiful moment.

When Phil and Keely finally got together

Speaking of everyone’s favorite Disney Channel couples, Phil and Keely from Phil of the Future were 100% meant to be. Their friendship was filled with tense moments where we all hoped they would finally admit they had ~feelings~ for each other. That all came to a head in the season finale, and oh boy, did we cry. Phil’s family fixes their time machine, and they realize they have to go back to their century. Phil and Keely admit they love each other and share a passionate kiss in front of the whole school. Phil’s family leaves in their time machine, and we were all forever left wondering what could have been.

When Cadet Kelly has to save her dad’s life

Finally, we have another legendary Disney Channel Original Movie, Cadet Kelly. In this movie, we got to see Hilary Duff branch out from her role and Lizzie McGuire and play a young girl who gets sent to military school. The most dramatic part of the movie? When Kelly’s ridiculous (it’s true) father fell to his near-death down a cliff. Kelly repels down to save him. Her step father, who sent her to military school in the first place, hugs her, and thus marks the beginning of their close new relationship.

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