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A Timeline of Jason Aldean’s Controversies: Blackface and Confederate Flags

Jason Aldean’s debut single, 2005’s “Hicktown,” arrived on country radio like a kick in the teeth, blending hard rock with country music and lyrics that unabashedly celebrated a certain type of rural life: “You can see the neighbor’s butt crack nailing on his shingles/and his woman’s smokin’ Pall Mall’s, watchin’ Laura Ingalls,” he sang.

“Hicktown” was an overnight success, a Top 10 hit on Billboard’s Hot Country chart and a crossover pop hit on the Hot 100. And the singles that followed were also mostly radio smashes, many of them pushing country music’s boundaries by incorporating elements of hard rock, like “Crazy Town,” and hip-hop, the breakout “Dirt Road Anthem.”

But as the Macon, Georgia, native inched closer and closer to Nashville superstar status, he also slowly leaned into the more odious of conservative viewpoints and right-wing politics, culminating with a Trump bromance — golf outings! New Year’s Eve parties! Mar-A-Lago visits! — that began in earnest in 2021. Since then, he’s espoused right-wing ideologies from anti-vaccine theories to stolen election conspiracies. There’s also been some racist messaging, casual misogyny, and, most recently, a song and music video that are, at best, small-minded and, at worst, racist.

In the video for Aldean’s single “Try That in a Small Town,” the singer performs in front of a courthouse in Columbia, Tennessee, the site of a lynching in 1927 and a race riot in 1946. The lyrics reference “good ol’ boys” ready to fight criminals who stick up liquor stores and disrespect cops and the American flag. Aldean even threatens to use a gun his grandfather gave him. (Aldean has denied accusations that the song is “pro- lynching.”)

Although “Try That in a Small Town” may seem on the surface to be the peak of edgelord behavior, Aldean has spent the past few years becoming more vocally far right, even after telling Rolling Stone in 2016 that he steers clear of politics: “That’s one subject I do stay away from. Politics is a no-win.” Here’s a timeline of how Aldean has become country music’s lightning rod.

September 2015: Jason Aldean can’t tell female singers apart

In an interview with Washington Post in September 2015, Aldean was asked about the lack of female singers on country radio; gender parity has continued to be a struggle in the ensuing years. While he didn’t posit to know why that is the case, he ventured to theorize that a lot of women sound the same.

“I feel like a lot of times female singers, to me, when they’re singing – and I’ll probably kick myself for saying this – a lot of times, it just seems like I can’t distinguish one from the other sometimes if I just listen to them, you know?” Aldean told the newspaper. “A lot of times they just sound really similar to me. And then you have some that come out like a Carrie [Underwood] or Miranda [Lambert] or somebody like that, that really has a different, distinctive sound to their voice, then it’s like, oh, OK, you can tell them apart all of a sudden.”

October 2015: Aldean wears blackface for Halloween

Jason Aldean had already logged two Number One and several multi-platinum albums by 2015, the year he decided to dress as Lil Wayne for Halloween, according to The Guardian. His costume included a red bandana, a wig of braided hair, and blackface. Nearly a year later, the singer offered a qualified apology to anyone who found it “disrespectful” in a Billboard interview. “Me doing that had zero malicious intent,” he said. “I get that race is a touchy subject, but not everybody is that way. Media tends to make a big deal out of things. If that was disrespectful to anyone, I by all means apologize. That was never my intention.”

2015 – 2019: Aldean wears a Confederate flag shirt onstage

As Americans have taken stock of their country’s past and the generational trauma that has lasted since the Civil War, more and more people have recognized the Confederate flag as a symbol of racism, oppression, and support of slavery. In 2015 — in the wake of the racially motivated mass shooting in Charleston, South Carolina — several musicians who had previously used the symbol on their merchandise, calling it an emblem of Southern pride, changed their minds and removed them. Aldean nevertheless continued wearing the flag, which was part of a Hank Williams Jr. T-shirt; the image has been floating around online since 2018, according to a TinEye search. That same year, a purportedly official Aldean tour shirt that included the Confederate flag was available to purchase online. He also wore an Alabama shirt with a Confederate flag on it in 2019. News reports from 2015 and from 2017 suggest his association with the flag goes back years earlier.

October 2020: Aldean poses maskless at Disney World

In July 2020, a little less than four months after Covid lockdowns went into effect, Disney World reopened with protocols including temperature checks at the entrance and a mandate requiring people to wear masks. When Aldean brought his family there that fall, though, they flounced the precautions. Aldean posted a photo he later deleted in October that showed him and his wife, son, and three daughters smiling sans face coverings. “Perfect day with my whole crew today at Walt Disney World,” he wrote. “There is nothing like seeing your kids faces when u walk in that place.” When a fan commented on the photo asking where the masks are, he replied: “Chill out lady. They are in our pocket. We took them off for 5 seconds to take the pic. Believe me, Disney didn’t give us a ‘free pass’ not to wear them. We had them on all day just like everybody else.”

2020 – 2023: Aldean proudly aligns with Trump

Aldean is a proud conservative and Donald Trump supporter. As The Tennessean reports, the country star discussed his political stance in 2020 while visiting Trump’s Mar-a-Lago golf course in Palm Beach, Florida. He and his influencer wife, Brittany, have also rung in the last couple of new years at the former president’s resort. In 2022, the couple attended Trump’s annual New Year’s Eve gala and posed with him for a photo opp, which included pictures and video of Jason and Trump playing golf together.

“Well, this New Year’s was the best of all time,” Jason Aldean captioned the snap on Instagram. “I got to spend a couple days with the G.O.A.T…… this man is unbelievable and I wish u all could see what he does behind the scenes. #classact”

They reprised their gala attendance, which is by invitation only for 2023 NYE, as Country Now points out. The couple once again shared photos from the night on Instagram. And apparently, the lovefest is mutual: Trump also introduced a performance by Aldean, who sang Uncle Kracker’s “Drift Away.”

“So, speaking about first, we have a man… we played golf yesterday, he’s a fine golfer but he’s much better with the guitar,” Trump said. “He’s much better with the most beautiful wife I’ve ever seen, and the reason he’s got this incredible wife is that he’s the Number One country star and he’s agreed to come up and sing for us tonight. He’s also a fantastic guy, he is a great guy. They love him in country land but they love him all over the world. He’s the Number One country star, Jason Aldean.”  

 Aldean also seemed to buy into election fraud conspiracies after the November 7th call for Joe Biden as president, posting a blue-and-red graph equating Biden and Trump’s urine streams with their vote counts (Biden’s dramatically bounced ahead, an allusion to his late surge in the count, which Trump claimed was a sign of fraud).

October 2021: Jason Aldean defends wife Brittany’s anti-Biden stance

After backlash stemming from Brittany Aldean posting photos wearing an “Anti Biden Social Club” shirt alongside photos of her children sporting “Hidin’ From Biden” ones, husband Jason defended her.

“I will never apologize for my beliefs or my love for my family and country,” Aldean posted on Instagram, sharing a photo of himself in front of an American flag. “This is the greatest country in the world and I want to keep it that way. #unapologetic #phoenixwasfire.”

August 2021: Aldean praises maskless concertgoers before Covid vaccines were widely available

Video posted on August 16, 2021, shows Aldean talking to a crowd on his Back in the Saddle Again Tour. “The coolest thing about all this, the coolest thing about right now, is that I’m looking out at all you guys and I don’t see one fucking mask,” he said, to cheers from the audience. The crowd started chanting, “U.S.A.! U.S.A.!” and Aldean continued, “I’ve had just about enough of that shit.” The FDA approved the first Covid vaccine on August 23, 2021.

September 2022: A PR company cuts ties with Aldean over his wife’s transphobic social media post

On August 23, 2022, Brittany Aldean posted a video to Instagram showing her putting on her makeup with the caption, “I’d really like to thank my parents for not changing my gender when I went through my tomboy phase.” Country artists Cassadee Pope and Maren Morris spoke out against Aldean’s sentiment. “Sell your clip-ins and zip it, Insurrection Barbie,” Morris commented at the time. On September 1, Aldean’s longtime Nashville publicity firm announced it would end its relationship with the artist.

October 2022: Aldean trolls Maren Morris onstage at his Nashville concert

During his headlining performance at Nashville’s Bridgestone Arena in October of last year, Aldean brought out a round of surprise guests, including Miranda Lambert and Morgan Wallen. While introducing one of his surprise guests, Aldean suggested it might be Maren Morris — who publicly battled with Aldean’s wife Brittany over a transphobic comment Aldean’s spouse had made online. The comment was red meat for the crowd, who let loose in a round of boos.

July 2023: Jason Aldean’s “Try That in a Small Town” suffers backlash, pulled from CMT

Aldean released the video for “Try That in a Small Town,” which features the singer performing in front of a courthouse, while footage portraying protests (some in Canada as it turns out) as violent and lawless flickers by. The backlash was swift, and included country-music network CMT pulling the music video from its rotation. Music fans and musicians alike, including Sheryl Crow, slammed him. “I’m from a small town,” Crow wrote on Twitter. “Even people in small towns are sick of violence. There’s nothing small-town or American about promoting violence. You should know that better than anyone having survived a mass shooting. This is not American or small town-like. It’s just lame.”


Aldean dismissed criticism of the song. “In the past 24 hours I have been accused of releasing a pro-lynching song (a song that has been out since May) and was subject to the comparison that I (direct quote) was not too pleased with the nationwide BLM protests,” he tweeted. “These references are not only meritless, but dangerous. There is not a single lyric in the song that references race or points to it – and there isn’t a single clip that isn’t real news footage – and while I can try and respect others to have their own interpretation of a song with music – this one goes too far.”

He added: “Try That In A Small Town, for me, refers to the feeling of a community that I had growing up, where we took care of our neighbors, regardless of differences of background or belief. Because they were our neighbors, and that was above any differences. My political views have never been something I’ve hidden from, and I know that a lot of us in this country don’t agree on how we get back to a sense of normalcy where we go at least one day without a headline that keeps us up at night. But the desire for it to – that’s what this song is about.”

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