Dave Portnoy Compares Zach Bryan to Diddy in Scathing Diss Track

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Dave Portnoy wasn't kidding when he said he would "come back spitting bars" after YouTube took down his Zach Bryan diss track.

On Sunday, November 10, the Barstool Sports president dropped another diss track aimed at the country music star — this time without his BFFs podcast co-host Josh Richards. The single "Country Diddy" compares Bryan to Sean "Diddy" Combs, who was arrested on September 16 on indictments of sex trafficking, racketeering, and transportation to engage in prostitution.

"All the NDAs, you sound like country Diddy," Portnoy raps on the track. He addresses the initial video getting taken down with lyrics like, "Butter cup really thought that he could shut me up, someone tell your cheap lawyers I don't give a f***."

Barstool founder and CEO Dave Portnoy is seen before the Florida Atlantic Owls and Loyola (Il) Ramblers game in the Barstool Invitational on November 8, 2023 in Chicago, Illinois. In November 2024, he released 'Country... Michael Hickey/Getty Images

The song is another criticism of the "Something in the Orange" singer following his breakup with Brianna Chickenfry (real name Brianna LaPaglia), who also co-hosts the BFFs podcast with Portnoy and Richards.

She and Bryan began dating in July 2023, but split in October 2024, following rumors that the country singer had been cheating on her with women he met on dating apps like Raya. LaPaglia was reportedly "blindsided" by the breakup, with a source telling Us Weekly, "They had just moved in together in the spring, and she changed her whole life to accommodate his."

The release comes after Portnoy's initial diss track with Richards — "Smallest Man," seemingly inspired by Taylor Swift's The Tortured Poets Department song "The Smallest Man Who Ever Lived," as Portnoy is a fan — was taken down from YouTube due to a contract Richards had signed with Warner Music Group in 2020. Since Warner has the rights to Richards' music — and Bryan is also a client of theirs — that allowed them to pull the track.

Portnoy took to X (formerly Twitter) on Wednesday, November 6 to give an update on "another twist in the smallest man diss track saga #davesversion." He shared his frustration at the song being taken down, while also promising more would be coming. "You're in the mud, you got me mad. I'm going to have to get in the booth. I thought it was going to be one-and-one. I don't care. I'll keep spitting."

"Country Diddy" didn't pull any punches, slamming Bryan's alleged offer of $12 million and a New York City apartment for LaPaglia to keep mum about details surrounding their relationship. "Offered Bri $13 mil, just to shut her trap, then she turned around and said 'shove it up your a**," Portnoy raps.

Personal insults were not off the table, with lyrics like, "Cheeks like Bugs Bunny, hair like Doug Funny, Go buy a toupée with your little hush money." He also called Bryan an alcoholic on the track, rapping, "Alcoholic needs help, he's out of his depth, but if you tried 12 steps, you would get out of breath."

"Wonder why you're demonized, with your little demon eyes?" Portnoy continued, adding, "I made a list about how you're such an evil guy. And this is your 13 millionth reason why." Referencing his first diss track, Portnoy raps, "Of course the world's a giant to the smallest man alive."

To prevent the song from getting taken down again, Portnoy was the only one rapping on this track, and he made it clear he's the one Bryan needs to be worried about. "You ruin people's lives, then hand out NDAs. I'm the one person you can't pay to go away." Portnoy also accused Bryan of stealing LaPaglia's Bronco, rapping, "Heard a little ditty 'bout sealing Bri's truck, I'll give you 80 bands, you dirty little f***."

Since their October split, LaPaglia has detailed the emotional abuse she allegedly experienced while dating Bryan. "He's screaming at me and then you wake up, it's the apology, it's the, 'I'm going to be better like I need you in my life.' I don't expect people to understand emotional abuse if you haven't been through it," she told the BFFs podcast audience.

"The last year of my life has been the hardest year of my life dealing with the abuse from this dude. I'm still scared right now because I'm scared of him. My brain's rewired and I'm scared to make him mad, and last week, I didn't want to talk about it 'cause I was scared," LaPaglia shared.

Bryan has not publicly responded to his ex LaPaglia's claims. However, an Instagram Story he shared on Thursday, November 7 did have fans wondering if he was vaguely trying to address the situation.

He reposted an image shared to Jack Kerouac's estate's official Instagram account, which featured a quote from his novel, On the Road. The quote read, "I didn't know what to say. I felt like crying, Goddammit everybody in the world wants an explanation for your acts and for your very being."

Since Bryan had his comments turned off, many flooded the comments section of the Kerouac estate to share their thoughts on the country singer.

If you or someone you know are experiencing domestic abuse — this includes emotional abuse — please call the National Domestic Violence Hotline at 1-800-799-7233 for confidential support.