If you grew up during the golden age of 2010s Disney Channel, you basically spent every Friday night on a penthouse balcony in New York City. We all remember the setup: a bubbly nanny from Texas, four wealthy kids, a giant lizard, and a sarcastic butler. But years after the final episode of Jessie aired in 2015, the conversation shifted from silly subplots to the actual relationship between Debby Ryan and Skai Jackson.
Was it a sisterly bond or a toxic workplace? Honestly, the internet has spent a decade trying to figure that out.
The rumors started small—mostly Tumblr whispers and weirdly specific tweets. Then they exploded. People started looking for "clues" in every interview and red carpet photo. Even today, in 2026, fans are still dissecting clips of these two, trying to find proof of a feud that might have never been as dramatic as we thought.
The Nanny and the "Princess": Where it Started
Debby Ryan was already a Disney veteran when Jessie premiered in 2011. She’d come off a massive run on The Suite Life on Deck as Bailey Pickett. She wasn't just the star of Jessie; she was a producer and a mentor. Skai Jackson, on the other hand, was just nine years old when she stepped into the role of Zuri Ross.
That age gap is huge. Nine years.
In the beginning, it looked like total adoration. Skai told Clevver TV back then that Debby was "fantastic" and had "good acting skills." Debby would post photos of "snuggle time" with Skai before live tapings. It was the typical "big sister, little sister" narrative that Disney loves to market.
But things changed as the show progressed.
💡 You might also like: Birth Date of Pope Francis: Why Dec 17 Still Matters for the Church
Working on a soundstage for 12 hours a day isn't exactly a normal childhood. While Debby was navigating the pressures of being a young adult executive in a massive corporate machine, Skai was growing up in the spotlight. By 2015, the "snuggle" posts stopped. The vibes felt... off.
The Infamous "Secret Twitter" and the Tumblr Post
The real drama hit the fan around the time the show was wrapping up. Rumors began circulating that Skai Jackson had a secret "finsta" or a private Twitter account where she allegedly vented about Debby bullying her on set.
No one ever produced a verified screenshot of this account. Not one.
Still, the internet took it and ran. It got so loud that Debby Ryan actually addressed it in a now-famous Tumblr post. She didn't name Skai directly—she’s too savvy for that—but she wrote about "parental maliciousness" and the importance of "emotional security" for child actors.
"I won't speak on specific people, because it's unprofessional to slander coworkers online," Debby wrote.
She basically implied that there was tension, but she framed it as a result of the environment rather than a personal vendetta. It was a classic PR move: acknowledge the fire without pouring gasoline on it.
📖 Related: Kanye West Black Head Mask: Why Ye Stopped Showing His Face
The "Musty" Edit and the TikTok Era
Fast forward to 2020. The world is in lockdown, and everyone is on TikTok. A fan asked Skai point-blank if she hated Debby.
Skai’s response? "Girl no, love her."
Simple. Case closed, right? Nope. A troll took that video and edited the caption to say something incredibly derogatory about Debby. It went viral. Skai had to jump back into the comments to clarify that she never said that, pleading with people to stop making fake replies.
It’s kind of wild how much people want them to hate each other. Maybe it’s because we love a good "Disney star downfall" story, or maybe it’s because their public personas are so different. Debby has transitioned into this indie-cool, slightly eccentric actress (and the internet's favorite meme for that Radio Rebel hair tuck). Skai, meanwhile, became the "Queen of Feuds" for a while, famously clashing with Azealia Banks and Bhad Bhabie.
Why the rumors persist in 2026:
- The "Blurred Face" Photo: There was a throwback photo Skai posted where Debby’s face was allegedly cropped or blurred. Fans saw this as the ultimate shade.
- Lack of Public Interaction: Unlike the High School Musical or Wizards of Waverly Place casts, you don't see Debby and Skai having "reunion dinners" every few months.
- The Bunk'd Transition: When Jessie ended, Skai, Peyton List, and Karan Brar moved to the spinoff Bunk'd. Debby didn't. She went to Netflix to do Insatiable. This natural career split looked like a "breakup" to fans.
Looking at the Facts Today
Let's be real for a second. If you worked with someone when you were 10 and they were 19, would you be best friends ten years later? Probably not. You’d probably just be "work friends" who lost touch.
Debby Ryan is now married to Josh Dun from Twenty One Pilots. She’s focused on film and fashion. Skai Jackson has faced her own set of adult challenges, including a widely reported legal incident in 2024 involving a domestic dispute. Their lives have moved in completely different directions.
👉 See also: Nicole Kidman with bangs: Why the actress just brought back her most iconic look
There is zero evidence of an active feud. There’s also no evidence of a deep friendship.
It’s more likely that they were two people in a high-pressure environment who simply didn't click on a deep level. Hollywood is a workplace. Sometimes you love your coworkers; sometimes you just want to finish the scene and go home.
Moving Past the Nostalgia
If you're looking for a smoking gun, you won't find it. What you will find is a nuanced story about the reality of being a child star.
The "drama" between Debby Ryan and Skai Jackson is a lesson in how the internet creates narratives out of thin air. We project our own feelings onto these stars because we feel like we grew up with them. We want the Ross family to be real, but they were just actors playing a part.
Next Steps for Fans:
If you want to see what they're actually up to now, skip the gossip threads. Check out Debby Ryan’s recent work in The Resort or her fashion collaborations. For Skai, her 2019 book Reach for the Skai actually gives a lot of insight into her perspective on growing up in the industry. Stop looking for the shade and start looking at the careers they've managed to build despite the "Disney Curse."
The penthouse is empty, guys. It’s time to let the 2015 rumors stay in 2015.