Brianna Chickenfry and Grace O'Malley: What Really Happened to the Internet’s Favorite Duo

If you spent any time on TikTok between 2020 and 2024, you probably felt like you knew Brianna Chickenfry and Grace O’Malley personally. They were the blueprint for the "chaotic best friend" brand. One was the unfiltered, party-hardy visionary who manifested a career out of thin air; the other was the hilarious, grounding force who seemed to be the only person capable of keeping the wheels on the bus.

Then, the wheels didn't just come off. They flew into orbit.

The friendship between Brianna LaPaglia (known to everyone as Chickenfry) and Grace O’Malley wasn't just a personal bond—it was a business empire at Barstool Sports. But by early 2026, the dust has finally settled on a saga involving country music superstars, $12 million NDAs, and a public falling out that left fans picking sides like it was a digital civil war. Honestly, it’s a lot to process.

The Rise of PlanBri and the 5th Grade Pact

The story starts long before the Barstool microphones and the New York City high-rises. Brianna and Grace were childhood friends from Rockland, Massachusetts. They’ve been in each other's pockets since the fifth grade. That history is exactly why their eventual split hit the internet so hard. You don't just "break up" with a friend you've known since you were ten without some serious scars.

In 2020, Brianna landed an internship at Barstool Sports after her "hangover" TikToks went nuclear. She moved to New York and, in a move that honestly defines her character, she dragged Grace along with her. She literally made up jobs for Grace—manager, producer, whatever—just to get her foot in the door. Eventually, Dave Portnoy saw the vision, and PlanBri Uncut was born.

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For a couple of years, it was magic. They were the girlies everyone wanted to drink a White Claw with. They shared stories about horrific teen experiences in Atlantic City and the awkwardness of navigating their twenties. But fame is a weird drug, and it affects people differently.

The Zach Bryan Factor: Where Everything Went South

You can’t talk about Brianna Chickenfry and Grace O’Malley without talking about Zach Bryan. For a long time, the rumors were just whispers. Fans noticed that Grace was rarely seen with Zach. The "vibe" was off.

When Brianna and Zach eventually split in October 2024, the floodgates opened. Brianna went on the BFFs podcast and dropped bombs. She claimed Zach offered her $12 million and a house just to sign an NDA and stay quiet about their relationship. She turned it down. She also claimed Grace wasn't supportive enough during the relationship's toxic low points.

According to Brianna, Grace knew everything that was happening behind the scenes but didn't defend her when the internet started attacking her. Brianna felt like the public was lifting Grace up specifically to tear Brianna down.

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Grace, for her part, had a very different experience. She claimed she was blindsided when Brianna announced the end of PlanBri Uncut. She even shared that she had bit her tongue for a year out of respect, only to find out through social media that Brianna was "working on a new version" of the show without her.

Life in 2026: The Aftermath

Fast forward to today. It’s early 2026, and the landscape has changed completely.

Zach Bryan is married to Samantha Leonard—they tied the knot in Spain on New Year's Eve. He recently released a song called "Skin" that feels like a total scorched-earth anthem toward Brianna. He sings about taking a blade to his old tattoos (they had matching "how lucky are we" ink) and mentions how his ex "talks badly about all her friends." It's a clear nod to the Grace fallout.

Brianna hasn't stayed quiet. She’s been posting cryptic TikToks using Taylor Swift lyrics to clap back. She’s also leaned into her solo career. PlanBri Uncut is back, but it's just Brianna now. She’s called it a "full circle" moment, returning to the solo format she started in her college dorm. She even did a stint on Special Forces: World’s Toughest Test, trying to prove she’s more than just a "party girl" headline.

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Grace O’Malley, meanwhile, has had a massive "glow-up." She left Barstool and joined Alex Cooper’s Unwell Network. She’s touring as a comedian and finally has a space where she isn't "Brianna’s sidekick." In a 2025 interview with Theo Von, she called the situation a "rough patch" and said she still loves Brianna, but they are clearly living in two different worlds.

Why the Internet Can't Let It Go

The fascination with Brianna Chickenfry and Grace O'Malley comes down to relatability. Everyone has that one friend they outgrew or that one relationship that poisoned their social circle.

• The Power Balance: People loved Grace because she felt like the "normal" one, while Brianna was the one "making it." When that dynamic shifted, it felt personal to the viewers.
• The NDA Reveal: The $12 million figure changed the conversation from "influencer drama" to a serious discussion about control and silence in the industry.
• The Longevity: Growing up together creates a level of expectation. People feel like if a 15-year friendship can fail, anything can.

What We Can Learn from the Fallout

If you’re following this saga for more than just the tea, there are some pretty heavy life lessons tucked into the drama.

First, the "friendship vs. business" trap is real. Mixing your oldest bond with a high-stakes media contract at a place like Barstool is basically a ticking time bomb. Second, the way you handle a breakup—whether with a partner or a best friend—defines your public brand for years. Brianna chose transparency; Grace chose a "political" silence. Both paths have had massive consequences for their careers.

Next Steps for Fans and Observers:

To get the full picture of where they stand now, you should check out Grace O'Malley's solo episodes on the Unwell Network to hear her develop her own comedic voice. On the flip side, watching Brianna’s "exposé" episode on the BFFs podcast is essential for understanding the sheer scale of the Zach Bryan situation. Finally, pay attention to the lyrics in Zach Bryan's latest project, With Heaven on Top; it’s the closest we’ll ever get to his side of the story without an NDA getting in the way.