Morgan Wallen Smirks as He Sends Surprising Shoutout to His ‘Probation Officer’ [WATCH]

Country music sensation Morgan Wallen, 31, raised eyebrows this week during a candid and cheeky interview in which he gave a shoutout to his “probation officer,” appearing to make light of the legal troubles that followed his much-publicized 2024 arrest.

Wallen, who was charged after throwing a chair off a rooftop bar in Nashville, has since expressed remorse for his actions.

However, his latest comments are sparking renewed public scrutiny about whether he’s truly learned from the incident.

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The incident in question occurred in April 2024 at the grand opening of Chief’s Bar in Nashville, owned by fellow country star Eric Church.

Though Wallen wasn’t expected to attend the event, he showed up and soon after alarmed onlookers by hurling a chair from the rooftop.

The piece of furniture landed dangerously close to two police officers—just feet away from a potentially catastrophic outcome.

At the time, Wallen faced serious consequences: three felony counts of reckless endangerment and one misdemeanor count of disorderly conduct.

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Ultimately, those charges were reduced.

Wallen pleaded guilty to two misdemeanor counts of reckless endangerment and avoided jail time, instead receiving a sentence of two years’ probation, a $350 fine, and seven days in a DUI center.

Despite the serious nature of the incident, Wallen took a surprisingly lighthearted tone in a new appearance on Caleb Pressley’s Sundae Conversations YouTube series.

In an interview for Sunday Conversation, @MorganWallen addresses the important questions. pic.twitter.com/QSIR294Sy3

— American Country Music Chatter (@ACMC_Country) May 11, 2025

During the interview, Pressley asked, “Is this your first time here?” to which Wallen, grinning, replied, “Yeah… hopefully I don’t violate my probation by being here.”

Pressley, seemingly caught off guard, followed up: “Are you on probation right now?”

“Yeah… shout out to my PO,” Wallen responded, before bursting into laughter.

The moment, now making the rounds on social media, has been met with a mix of amusement and concern.

For fans who’ve seen Wallen navigate controversy before, the clip might seem like a red flag suggesting that his sense of accountability could be slipping.

Wallen’s arrest last year was not his first brush with controversy.

NEW: Footage released of Morgan Wallen launching a chair over the edge of a rooftop bar in Nashville.

According to the Metropolitan Nashville Police Department, the chair landed just 3 feet from their officers.

If convicted of the felony charges against him, Wallen could face… pic.twitter.com/4weIj577Yp

— Collin Rugg (@CollinRugg) April 9, 2024

But the seriousness of the chair-throwing incident—particularly the potential harm to police officers—drew sharp criticism from both media outlets and fans.

An anonymous source close to Wallen told People magazine at the time that the singer’s relationship with alcohol has long been a “problem that keeps coming back around.”

“Morgan is generally a nice, fun person to hang out with, but when he gets going he doesn’t know when to stop,” the source said.

In the immediate aftermath of his arrest, Wallen issued a formal apology on X (formerly Twitter).

“I didn’t feel right publicly checking in until I made amends with some folks,” he wrote. “I’ve touched base with Nashville law enforcement, my family, and the good people at Chief’s. I’m not proud of my behavior, and I accept responsibility.”

I have the utmost respect for the officers working every day to keep us all safe. Regarding my tour, there will be no change. -MW

— morgan wallen (@MorganWallen) April 20, 2024

“I have the utmost respect for the officers working every day to keep us all safe,” he added. “Regarding my tour, there will be no change.”

In what seemed to be a sign of real growth, Wallen stated last month during an appearance on Theo Von’s This Past Weekend podcast that he hasn’t been in a bar since the night of the incident.

“It’s definitely the best thing for me,” Wallen said. “I mean, if you’re using a bar as a specific example, that’s definitely, that’s definitely, the best thing for me.”

“I ain’t been in a bar since the last time I was in a bar that everybody knows about,” he added. “The most public time I was in a bar? That’s the last time I was in a bar.”

This admission seemed to underscore a newfound self-awareness, one that fans and critics alike had hoped would stick.

But his recent smirk-filled exchange with Pressley has cast a shadow of doubt on that progress.

One year ago today, Morgan Wallen was arrested after throwing a chair off the top floor of Eric Church’s bar. pic.twitter.com/0P90rAKDGY

— Country Central (@CountryCentral) April 8, 2025

Only time will tell whether Wallen’s probation period will reinforce meaningful change or be overshadowed by continued irreverence.

Public figures like Wallen wield significant influence, and with that comes the responsibility to handle personal missteps with humility and sincerity.

His apology and abstinence from bar settings suggest a man on the mend—but public perception is fragile, especially when humor is used to downplay serious matters.

As Wallen continues his tour and rebuilds his image, fans can only hope he remembers the weight of the incident and the people who could’ve been harmed.

A smirk and a shoutout might make for a viral clip, but accountability—and genuine personal growth—go far deeper.

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