Dave Portnoy blasts Zach Bryan for his hairline, height and 2023 arrest in diss track over Brianna breakup

Barstool Sports’ Dave Portnoy is ripping Zach Bryan over his hairline, height, a 2023 arrest and accusations of infidelity and sexually transmitted diseases and has escalated his public feud with the country singer by releasing a diss track.

Portnoy co-hosts a podcast with Bri Chickenfry (real name: Brianna LaPaglia), who dated Bryan from the summer of 2023 until last month, when he revealed their split on Instagram.

LaPaglia has since publicly claimed she was blindsided by the news, which prompted Portnoy and Barstool’s attacks.

“Itty bitt Zach, s***ty s****ty tats, ugly in the face, ain’t no cure for that,” Portnoy rhymes in one verse.

“How lucky is Bri to be free of ZB and his STDs?” Portnoy’s fellow rapper and podcast co-host Josh Richards sings.

Much of the music video revolved around Dave Portnoy (pictured) playing a cop

Bryan and LaPaglia (pictured in February) called it quits last month after a year together

Bryan and LaPaglia (pictured in February) called it quits last month after a year together

Portnoy (right) and Richards (left) lambasted Bryan for his height and his 2023 arrest

Portnoy (right) and Richards (left) lambasted Bryan for his height and his 2023 arrest

The song, titled ‘Smallest Man’, an apparent reference to a Taylor Swift song, lasts over five minutes and received a positive response online from Portnoy’s faithful Stoolies.

“Spit sticks Dave!” wrote one fan.

Another noted, “Portnoy’s flow has improved significantly,” suggesting this wasn’t the media mogul’s first attempt at rapping.

Other attacks in the diss track include a claim that Bryan’s “entire band” hates him, and a claim that Bryan has an alcohol problem.

“The way all your tweets look, I’d say you have a drinking problem,” one text read. “Such an alcoholic, alcohol has a ‘you’ problem.”

And then there was a verse about Bryan’s arrest in 2023 for allegedly interfering with a traffic stop. Portnoy and Richards not only shamed the singer for being detained, but also recorded embarrassing police-recorded audio of Bryan’s arrest.

Dave Portnoy accused Zach Bryan of being

Dave Portnoy accused Zach Bryan of being “STD positive” in the music video

Brianna, real last name LaPaglia, released a tearful video about the split last month

Brianna, real last name LaPaglia, released a tearful video about the split last month

Dave Portnoy previously got a hair transplant before making fun of Zach Bryan's hairline

Dave Portnoy previously got a hair transplant before making fun of Zach Bryan’s hairline

“I would get back in my truck right now if you would let me get out of these handcuffs,” Bryan is heard telling an Oklahoma Highway Patrol trooper in September 2023. “If you don’t, it will be a mistake, sir.”

Portnoy’s attacks on Bryan’s height and hairline were curious, as these are issues the 47-year-old aspiring rapper has faced himself.

Portnoy has even admitted to having a hair transplant in the past and can be seen on HairDr.com endorsing Leonard Hair Transplant Associates.

And then there’s Portnoy’s height, which he claims is 6-foot-1, although there’s still skepticism about that.

Regardless, Portnoy didn’t feel like his own stature stopped him from rapping about Bryan’s, who according to the Barstool founder is about 6-foot-4, or 6-foot-4.