If you’ve spent any time on TikTok or X over the last year, you’ve probably seen the phrase "smallest man" attached to country superstar Zach Bryan. It’s not just a dig at his height—though people definitely go there. It’s actually the centerpiece of one of the messiest, most litigious celebrity breakups we’ve seen in a long time.
The whole thing is a tangle of Taylor Swift references, Barstool Sports drama, and some pretty heavy allegations that have shifted how a lot of people view the "Something in the Orange" singer.
The origin of the Smallest Man Zach Bryan label
Honestly, the "Smallest Man" thing started as a weaponized reference. After Zach Bryan announced his split from Barstool personality Brianna "Chickenfry" LaPaglia in October 2024, things got ugly fast. Dave Portnoy, the founder of Barstool and Brianna’s boss, didn't just post a supportive tweet. He went for the jugular.
He dedicated Taylor Swift’s song, "The Smallest Man Who Ever Lived," to Brianna.
The choice was intentional. Zach had previously caught heat for a late-night tweet where he claimed Kanye West was better than Taylor Swift—a take he later apologized for, claiming he was "tipsy." By using a Swift song to label him, Portnoy was hitting Zach where it hurt.
But it didn't stop at a playlist dedication. Portnoy and Josh Richards actually recorded and released a full-blown diss track titled "Smallest Man."
What was actually in the diss track?
The song "Smallest Man" was basically a five-minute laundry list of every rumor and grievance surrounding Zach Bryan. It wasn't subtle.
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They went after his height, alleging he’s much shorter than he claims on his Raya profile. They mocked his "shitty tats." But the heavier stuff involved allegations of infidelity and "love bombing."
"Caught your pants on fire / Tinder, Bumble, Raya / Knew you was a liar."
The lyrics even brought up an old controversy involving leaked texts about STDs, which really turned the volume up on the drama. For a few days, the song was everywhere—until Zach’s legal team and record label, Warner Music Group, stepped in.
The legal battle and the $12 million NDA
This is where the story gets darker than just some internet beef. Brianna eventually went on the BFFs Podcast and dropped a bombshell: she claimed Zach’s team offered her a $12 million non-disclosure agreement (NDA) to never speak about their relationship.
She turned it down.
She described a relationship that was "emotionally abusive," claiming Zach would freak out over things as small as her singing a Morgan Wallen song or her choice of clothing at the Golden Globes. She alleged that he isolated her from her friends and family, and that the "perfect" guy fans see on stage wasn't the guy she lived with.
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The "Smallest Man" label shifted from a joke about his stature to a commentary on his character.
Warner Music and the "Great Takedown"
When the "Smallest Man" diss track hit Spotify and YouTube, it was almost immediately scrubbed. Most people thought it was a simple copyright claim because the song used a parody of a Zach Bryan melody at the end.
Portnoy tried to re-upload it without the parody, but it got yanked again.
It turns out there was a weird corporate snag. Josh Richards, who co-hosted the track, was actually signed to a deal with Warner Music Group—the same label that represents Zach Bryan. Basically, the label "owned" Josh’s musical output and used that leverage to kill the song that was trashing their biggest country star.
Portnoy, being Portnoy, vowed to "die in the booth" and keep fighting, but the original track remains hard to find on official platforms today.
Why it still matters in 2026
You’d think after a year, people would move on. But Zach Bryan just released his sixth studio album, With Heaven On Top, and the song "Skin" has reignited the whole "Smallest Man" conversation.
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In "Skin," Zach sings about taking a blade to his old tattoos—a direct reference to the matching ink he and Brianna got.
"I’m taking a blade to my old tattoos. I’m draining the blood between me and you."
Brianna’s response? She posted a TikTok lip-syncing to Taylor Swift (again), basically laughing off the fact that he’s still writing songs about her while he’s now married to Samantha Leonard.
It’s a bizarre cycle. Zach tries to move on by getting married on New Year's Eve in Spain, but then he drops "Skin," which brings the "Smallest Man" allegations back to the front page of Google.
What we can learn from the Smallest Man saga
If you’re following this for the gossip, there’s plenty. But if you’re looking for the "why," it’s really about the shift in how celebrity breakups work.
The old way was to sign the NDA, take the money, and stay quiet. Brianna choosing to turn down $12 million to tell her "truth" changed the power dynamic. It showed that for modern influencers, "brand authenticity" is sometimes worth more than a massive lump sum.
Actionable Insights for Fans and Observers:
- Check the Lyrics: If you’re listening to With Heaven On Top, pay attention to the tracks "Skin" and "Plastic Cigarette." They offer Zach's side of the "moving on" narrative, even if they feel a bit defensive.
- Understand the NDA Culture: This situation highlighted how common NDAs are in country music. Several of Zach's other exes, like Rose and Deb Peifer, have hinted at similar experiences but have largely remained quiet.
- Separate Art from Artist: It’s okay to like the music while acknowledging the "Smallest Man" controversy. Most fans are currently grappling with the fact that his "vulnerable" songwriting might contrast with his private behavior.
The drama isn't going anywhere. As long as Zach Bryan keeps posting (and deleting) cryptic tweets and Brianna keeps her podcast microphone on, the "Smallest Man" saga will continue to be a case study in how fame, ego, and Taylor Swift lyrics can wreck a reputation.