The Shady Side Of Zach Bryan

In September 2023, Zach Bryan capped off his meteoric rise from a virtual unknown to a breakout country hero in the space of just four years when his eponymous fourth album reached the top of the Billboard 200. He initially appeared to be an entirely unproblematic chart-topper, too, with barely a whiff of a scandal or controversy surrounding him at the time.

Of course, that all changed within days, thanks to a controversial encounter with an Oklahoma cop, which appeared to open the floodgates. Indeed, ever since his brush with the law, Bryan has continually made headlines not for his gritty blend of alternative country, Americana, and heartland rock but for various questionable comments and behaviors. From suspect dating habits and beef with Swifties to family rebellions and canine snubbing, not to mention damaging claims of emotional abuse, here's a look at 13 times the "Something in the Orange" hitmaker got super shady.

Zach Bryan was famously close to his late mother, Annette, who sadly died following a struggle with alcoholism in 2016. His 2019 debut album was titled after her middle name, DeAnn, after all. Or how he described her as "An Oklahoma sweetheart, homecoming queen cheerleader, like a small-town freaking famous person almost" in a chat with The New York Times.

So, it was perhaps little surprise that when his parents divorced, and his father Dewayne — who he then permanently resided with — found a new love, the teenage Bryan found it hard to adapt. In fact, the future country star, who'd already shown signs of rebellion, ended up dramatically falling out with his dad and stepmom weeks before he was enlisted in Navy boot camp.

"He called my wife some names and he put me on my butt," Dewayne told the same newspaper about the reason behind the major beef. "He's tougher than nails." Thankfully, all parties eventually managed to put the turmoil behind them and now have a much less turbulent relationship.

Zach Bryan's joy at scoring his first Billboard 200 chart-topper in 2023 was soon curtailed when, later that same week, he was arrested for obstructing a law officer in Oklahoma.

The drama started when the country singer's private security was pulled over in their SUV for speeding. Bryan, who was behind the wheel of a following pickup truck, also stopped and, in a fit of impatience, soon walked up to Highway Patrol Trooper Ben Bertram to ask exactly what the delay was. Despite being warned about his behavior, the "Dawns" singer failed to comply with orders to get back in his vehicle on two occasions and was subsequently put in handcuffs and taken to the nearest station.

Bryan later apologized for his conduct on Instagram, telling followers (via Entertainment Weekly), "I support law enforcement as much as anyone can, I was just frustrated in the moment ... Prayers we can all move on from this and prayers people know I'm just trying the best I can, I love you guys and I am truly sorry to the officers." This was also the second time in three days that Bryan had gotten into trouble with the law. The singer-songwriter later revealed that he'd received similar treatment after failing to give his home address after being stopped by police.

Zach Bryan entered into his first country music feud in early 2024 when he threw some shade at fellow troubadour Walker Hayes. The drama began when the former questioned why Hayes' hit "Fancy Like" received more airplay than the song he believed it blatantly stole from.

"Imagine being radio (whoever the hell that is), hearing [Tyler Childers'] "Shake the Frost" and being like, 'No no let's go with the Applebees song,'" Bryan tweeted (via Billboard), referring to Hayes' Tik-Tok assisted smash which climbed the upper reaches of the Hot 100 three years earlier.

Quite why Bryan felt the need to criticize the track so long after its release remains a mystery. But Hayes didn't take things lying down. Indeed, in what briefly became Nashville's answer to Drake vs. Kendrick Lamar, the singer-songwriter uploaded a diss track to Instagram featuring the lyrics, "Felt like throwing punches/I just held 'em back/Because Jesus didn't die for me so I could fight with Zach." Perhaps wisely, the object of his ire decided against answering back.

It's fair to say that Zach Bryan's love life has been eventful of late. In the summer of 2020, he walked down the aisle with Rose Madden, only for the couple to dissolve the marriage a year later. In 2022, he entered into a year-long relationship with Deb Peifer. And then just two months after their split, the country star went public with another new love, "BFFs" podcast host Brianna 'Chickenfry' LaPaglia.

The timing of the latter romance led many to speculate that both Bryan and LaPaglia had cheated on their former partners, for the pair had first met at the ACM Awards in May 2023, when they were both still apparently in committed relationships. And the podcaster didn't exactly help matters when that very same month she told Theo Von that she was "overlapping."

"I'm a relationship girl," LaPaglia admitted (via J-14). "There's an overlap usually, always an overlap." When asked whether this was simply another word for cheating, the interviewee responded, "They're calling it overlap now." The couple spent much of 2023 declaring their love for each other, with LaPaglia often joining Bryan on stage to perform the final song, "Revival," on his "Quitting Time" tour. Meanwhile, "28," a song from the 2024 LP "The Great American Bar Scene," is said to be a romantic dedication. Of course, as we all now know, things didn't stay loved up for too long.

Lots of hitmakers would be delighted if they discovered that one of their latest songs was being considered for pop radio. Zach Bryan, on the other hand, appeared to take the news that "Pink Skies" had been sent to the format as a stain on his reputation.

Just a few days after the taster from fifth LP "The Great American Bar Scene" premiered, U.S. Radio Updater tweeted that the single had been serviced by the country star's label Warner Records to US Pop Radio. "This is f***ed," Bryan subsequently responded (via Whiskey Riff), adding that he'd not approved this particular strategy. "I'm not a f***ng Pop artist, or country artist leave me out of this. PINK SKIES IS NOT A POP SONG!"

The account that had started all the drama later explained that they may have gotten things slightly wrong, and that "Pink Skies" wasn't being released as a single but just as a showcase for the album. Bryan appeared to accept this version of events and later said sorry (via Country Now) for "cursing so much earlier" over the "misunderstanding." This wasn't the last time that Bryan expressed dissatisfaction at being pigeonholed, though. In a Rolling Stone interview with Bruce Springsteen, he said, "I don't want to be a country musician. Everyone calls me it. I want to be a songwriter, and you're quintessentially a songwriter."

In October 2024, Zach Bryan posted an Instagram story in which, out of the blue, he revealed that he'd split from his girlfriend of more than a year, Brianna LaPaglia. "She has loved me unconditionally for a very long time and for that I'll always thank her," the "Heading South" singer explained (via USA Today) before asking fans to respect their privacy and apologizing for anyone he'd let down.

And no one appeared to feel more let down than LaPaglia herself. The podcaster quickly took to Instagram herself to tell followers that she'd been left "blindsided" by her ex-boyfriend's very public confirmation. "Gonna hop off social media for a while and attempt to heal privately, when I'm ready I'll be back and ready to talk," she added.

LaPaglia later posted a YouTube video in which she revealed that Bryan hadn't given her any warning about his statement and that she'd been left in tears for five consecutive days as a result. "How can you give someone everything and love them so unconditionally, like through stuff that you shouldn't ... How can you give every ounce of yourself to someone and be discarded of in a few days?" The "BFFs" co-host then reiterated that she wanted to heal privately. But followers didn't have to wait too long to get more juicy details.

In November 2024, just weeks after splitting from Zach Bryan in acrimonious circumstances, Brianna LaPaglia turned from co-host to interviewee on her hit podcast "BFFs" to spill the beans. And one of the most jaw-dropping revelations concerned how her former boyfriend tried to stop her from spilling the beans.

Indeed, LaPaglia told colleagues Dave Portnoy and Josh Richard that Bryan had offered her an astonishing $12 million if she signed an NDA promising not to talk about any aspects of their relationship. Unfortunately for the "Open the Gate" singer, he soon found out that some things can't be bought.

Although she admitted that she was left in two minds over whether to take the money, LaPaglia ultimately decided that her integrity was more valuable. "I was like, 'F*** you; I don't want your money,'" she explained (via Vulture). "But then I look at my family who obviously doesn't have money and comes from nothing and they are like, 'Take the money.' I feel so stupid if I don't take this money, but then I'm not going to be able to sleep at night if I take this dude's money."

In November 2024, Brianna Lapaglia gave a candid interview to the Barstool podcast she co-hosts, "BFFs," in which she accused her ex-boyfriend Zach Bryan of emotional abuse. She shared several examples to support her claims, too, including a date at the Golden Globes earlier that same year that ended in tears.

La Paglia revealed that Bryan, who she'd been dating since the summer of 2023, had taken umbrage with her sartorial choice, adding (via USA Today) that "he didn't want to date someone that presents themselves that way." The podcaster went on to blast the "Open the Gate" singer for ruining not only the night in question but also her own tour and her birthday.

"Everything good, anything good I did for me, he made sure to ruin it for me," she told co-hosts Dave Portnoy and Josh Richards before theorizing exactly why Bryan was so rude about her fashion: "He makes me believe that I have to change my image to keep up with his or something."

If you ever happen to find yourself in the same company as Zach Bryan, whatever you do, make sure you avoid belting out any tunes by Morgan Wallen. In her bombshell chat on the podcast "BFFs," Brianna LaPaglia revealed that her former boyfriend became enraged whenever she sang a song by his fellow country star.

"One morning, like, we were out the night before, and one morning I woke up, or I was like, scrolling TikTok, and 'Last night we let the liquor talk...' was stuck in my head," LaPaglia explained (via People) about one particular incident in their shared New York apartment, referring to Wallen's hit "Last Night." The podcaster then added that Bryan hit the roof: "Like, he could not believe, 'You're singing another man's song under my roof in this house that I own.'"

When asked by co-host Dave Portnoy whether Bryan had a specific problem with Wallen or just other singers in general, LaPaglia admitted she didn't know. However, the fact that she claimed Bryan also disapproved of her listening to Noah Kahan indicates it may not have been limited to Wallen.

The co-host of Barstool's "BFFs" podcast has been one of the country singer's most vocal detractors since the allegations made by colleague Brianna came to light. But it turns out that his beef may have been kickstarted several months before. And it was all over a backstage snubbing of his dog.

Indeed, in November 2024, Portnoy told his listeners (via Elite Daily) that four months earlier, he'd brought his beloved pooch Miss Peaches to a Bryan gig in Foxborough, Massachusetts, a companion that had previously been fully approved by the headliner himself. However, the podcaster became incensed when he saw the "High Road" singer relocating the dog without any warning.

"It pissed me off greatly in the moment," Portnoy remarked. "He's kind of like, 'Oh, I hope you don't mind. I'm just moving Peaches.' What am I going to say? I'm like, 'OK.' I have no idea to this day why he wanted to get Peaches out of that locker room." The canine owner then went on to claim that the substitute locker room was unsafe due to the amount of rubbish and equipment that was lying around.

Zach Bryan's apparent habit of moving on from relationships perhaps a little too quickly was further exposed in October 2024 when he was reportedly caught hitting the dating apps. This was the same month, of course, that the country star had acrimoniously split from Brianna LaPaglia after spending more than a year together.

In fact, just a few days after he revealed the conscious uncoupling, Bryan was reportedly discovered to have been using the exclusive dating app known as Raya, with his alleged relatively modest profile listing only his songwriter occupation, Tulsa birthplace, and mid-20s age. This particular development surprised both the user who stumbled across it and his legion of fans, with one tweeter commenting (via the Daily Mail), "Like it's not my business, I don't know a thing about their personal lives, but still men are WILD."

Shockingly, an anonymous insider also told Us Weekly that Bryan had actually been using Raya while he was still with LaPaglia. "[Brianna] was blindsided by Zach being on dating apps and dating around while they had been in a committed relationship," the source explained. "Someone sent her Zach's Raya profile and girls were reaching out about him dating around ... She changed her whole life to accommodate his. She's devastated."

It takes a brave, or some would say foolish, individual to risk incurring the wrath of Taylor Swift's army at a time when the "Shake It Off" hitmaker is the most dominant force in pop culture. Zach Bryan found that out to his cost when he drunkenly tweeted that the chart-topper was inferior to one of her fiercest rivals, Kanye West.

In 2024, the "I Remember Everything" singer posted, "Eagles > chiefs. Kanye > Taylor" on X formerly known as Twitter (via USA Today), with the first half of his post also throwing shade at the Kansas City Chiefs team that Swift's boyfriend Travis Kelce plays for. Unsurprisingly, the Swifties soon came after Bryan which perhaps explains why he soon issued a groveling apology.

"For the record guys I wasn't coming for Taylor the other night," Bryan explained in an Instagram post (via Rolling Stone). "I was drunkenly comparing two records and it came out wrong. I know there's a lot of stuff that clouds around Ye and I was speaking purely musically." The Japanese-born star then insisted that he's a big fan of Swift's music and that he hopes to tell her that in person one day. "Twitter gets me in trouble too much and I'd say it's best I stay off it," he added, having deactivated his account.

Zach Bryan's shady side may only have publicly come to the forefront in late 2024. But according to a report by Page Six, the country singer was apparently renowned in the industry for being something of a jerk long before Brianna LaPaglia's emotional abuse claims.

An anonymous source, who claimed to have allegedly spent time on tour with Bryan, described the "Something in the Orange" hitmaker as "a horrible person" before sticking the knife in further: "He's so mean to everybody on his team. He's just kind of an a**hole."

And he wasn't the only insider keen to spill the beans about what Bryan is like behind the scenes. "Nashville is a male bro-dominated town, women are 'the tomatoes in the salad,'" claimed another person seemingly in the know. "They get away with everything, there is no accountability."