Dave Portnoy doesn't just hold grudges. He marinates them. He puts them on gold-plated champagne bottles and waits for the perfect moment to pop the cork. So, when country music titan Zach Bryan allegedly blindsided Barstool’s own Brianna Chickenfry (Brianna LaPaglia) with a public breakup post, Dave didn’t just send a supportive text.
He went to the studio. He put on the headset. He became a rapper.
If you haven’t been following the absolute circus that is the Dave Portnoy diss track saga, you’ve missed one of the weirdest collisions of Nashville country, Barstool "stoolie" culture, and high-stakes legal drama. It isn't just a silly song; it’s a full-blown corporate war involving Warner Music Group, a $12 million NDA, and enough petty energy to power the Northeast power grid for a month.
The Smallest Man Alive vs. The Country Diddy
The whole thing kicked off in November 2024. Zach Bryan, fresh off a string of sold-out shows, announced on Instagram that he and Brianna were done. The problem? Brianna says she had no idea he was posting it. She was blindsided.
Dave Portnoy, who co-hosts the BFFs podcast with Brianna and Josh Richards, immediately went into "protective father/boss" mode. He dropped a track called "Smallest Man," a title clearly nodding to Taylor Swift’s "The Smallest Man Who Ever Lived." It wasn't subtle. The lyrics went after Bryan for allegedly being on Raya (the celebrity dating app) the day of the split and poked fun at his 2023 arrest for obstruction of justice.
"There’s something in the orange and it’s you behind these bars, b*tch."
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That’s a direct shot at Bryan’s massive hit, "Something in the Orange." Honestly, it’s the kind of line that makes you cringe and laugh at the same time. But the drama didn't stop at the lyrics.
Why the First Diss Track Kept Vanishing
You might have tried to find "Smallest Man" on Spotify or YouTube only to see a "content removed" message. Usually, when a song gets pulled, it's a simple copyright strike for a sample. But this was messier.
Dave initially thought Warner Music Group (WMG) was just being protective of Zach Bryan. Then the truth came out: Josh Richards, who was featured on the track, had signed a recording contract with WMG years ago. They literally owned his voice. Since WMG also represents Zach Bryan, they had the perfect legal weapon to kill the song.
Portnoy’s reaction was exactly what you’d expect. He didn't back down. He posted a video vowing to write "10,000 diss tracks" and "die in the booth" if he had to. He basically declared himself a one-man independent label fueled entirely by spite.
Entering the "Country Diddy" Era
When "Smallest Man" got nuked, Portnoy pivoted. He dropped a second song titled "Country Diddy." This one was even more aggressive.
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The title is a reference to the legal troubles surrounding Sean "Diddy" Combs, implying a level of "industry plant" behavior or controlling tendencies. In this track, Dave leaned heavily into the allegations Brianna made on the BFFs podcast—specifically that Zach Bryan’s team offered her a $12 million "hush money" NDA to never speak about the relationship.
Brianna turned it down. She chose her voice over the $12 million. That gave Dave all the ammunition he needed.
What the Lyrics Actually Say
- The NDA: Dave mocks the idea that Bryan tried to buy Brianna’s silence.
- The "Fraud" Narrative: Portnoy has repeatedly called Zach a "fraud" who pretends to be a humble working-man's poet while acting like a "thin-skinned" diva behind the scenes.
- The Taylor Swift Comparison: Dave even duetted TikToks pointing out that some of Zach’s melodies sound suspiciously like Taylor Swift songs.
It’s psychological warfare.
Is This Just a Marketing Stunt?
A lot of people think Dave is just doing this for clicks. Well, yeah. It’s Barstool. Everything is for clicks. But if you watch the footage of Dave in the studio, he’s genuinely angry. He feels Zach Bryan mistreated someone on his team, and in Dave’s world, that’s the ultimate sin.
Critics say it’s "corny" for a 47-year-old multimillionaire to be rapping about a country singer's breakup. They aren't wrong. It is corny. It's objectively ridiculous. But that’s the Barstool brand. They take a niche internet drama and escalate it until it’s a national headline.
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Zach Bryan has mostly stayed quiet, though he did delete his Twitter (again) shortly after the first track dropped. For a guy who writes songs about being tough and resilient, he seems remarkably bothered by a guy from Boston who eats pizza for a living.
What Happens Next for the Portnoy-Bryan Feud?
As we move through 2026, the dust hasn't totally settled. The "Country Diddy" track proved that Portnoy can bypass the major labels if he wants to. He doesn't need Josh Richards to keep the heat on.
There are rumors that Brianna herself might get in the booth for "Dave's Version" of the tracks. If that happens, the internet might actually break.
How to Keep Up With the Drama
If you're looking for the latest developments, don't look at the music charts. You won't find Portnoy there. Instead:
- Watch the BFFs Podcast: This is where the raw audio and the "behind the scenes" legal threats get aired.
- Follow Dave on TikTok: He usually leaks snippets of the songs there before they get hit with a DMCA.
- Check Brianna’s Instagram Stories: She’s the one living through the fallout, and she often provides the context that explains why Dave is being so aggressive.
The lesson here? Don't break up with a Barstool employee unless you're prepared to have a middle-aged man in a police costume rap about your dating life for the next three years. Dave Portnoy has the money, the platform, and most importantly, the lack of shame required to keep this going forever.
Actionable Insights:
If you're a creator or a brand watching this, the takeaway is the power of owned media. Portnoy can't be "canceled" or silenced because he owns the platform. While Zach Bryan has to answer to a label and a PR team, Dave just needs a microphone and a grudge. If you're following the legal side, keep an eye on how NDA "hush money" discussions are shifting in the public eye; Brianna's refusal of that $12 million has set a massive precedent for influencers in high-profile relationships.