5 Celebs That Regretted Going to Vegas

Las Vegas has long been the playground of the rich and famous, offering a glittering escape from reality with its neon lights, lavish hotels, and promise of excitement around every corner.

But for some celebrities, what happens in Vegas doesn’t always stay in Vegas—sometimes it follows them out the door and into the headlines.

From impulsive marriages to costly gambling sprees (even though many have hit it big in Vegas), here are five stars who likely wish they could get a do-over on their Sin City adventures.

Prince Harry’s Wild Weekend

Before settling down as a husband and father, Prince Harry was known for his rebellious streak. In 2012, the royal made headlines worldwide when photos surfaced of him partying naked in a VIP suite at the Wynn Las Vegas during a game of “strip billiards.”

What was meant to be a private weekend of fun quickly turned into an international scandal.

The infamous Vegas trip caused a royal uproar, with Buckingham Palace scrambling to control the damage after the compromising photos were published by TMZ and subsequently picked up by media outlets globally. Harry later addressed the incident in his memoir, expressing regret not only for his behaviour but also for the way it reflected on his position within the royal family.

While the prince has since matured and moved on from his party days, the Vegas incident remains one of the most notorious celebrity escapades in the city’s history and served as a harsh lesson about privacy in the digital age—even for those of royal blood, what happens in Vegas rarely stays there when smartphones are involved.

Britney Spears’ 55-Hour Marriage

Las Vegas has long been famous for its quickie weddings, but few have been as headline-grabbing as Britney Spears‘ spontaneous marriage to childhood friend Jason Alexander in January 2004.

After a night of partying, the pop princess and Alexander decided to tie the knot at the Little White Wedding Chapel on the Strip, with Britney wearing jeans and a baseball cap for the ceremony.

Reality hit hard and fast. Within 55 hours, lawyers for Spears‘ management had secured an annulment, claiming the star “lacked understanding of her actions.” The brief union became one of the most infamous celebrity wedding mistakes and an embarrassing chapter in Spears’ already tumultuous public life at that time.

Years later, Alexander would claim the marriage was genuine on Britney‘s part but that they were forced apart by her management team. Regardless of the truth, the impulsive Vegas wedding has followed both parties for decades, serving as a cautionary tale about Sin City’s particular brand of spontaneity.

Ben Affleck’s Gambling Controversy

Ben Affleck‘s love of poker and blackjack is well-documented, but his passion for high-stakes gambling led to a regrettable incident in Vegas in 2014. The Oscar winner was playing blackjack at the Hard Rock Hotel and Casino when security approached him and reportedly banned him from the blackjack tables for card counting—a technique that isn’t illegal but is frowned upon by casinos.

While Affleck initially tried to downplay the incident, it sparked widespread coverage about his gambling habits. In subsequent interviews, he admitted to having spent a significant amount of time learning card counting and acknowledged that what happened wasn’t his proudest moment. The incident forced him to confront public questions about potential gambling addiction, something he has repeatedly denied despite acknowledging his love for high-stakes games.

The Vegas controversy came at a particularly challenging time in Affleck‘s personal life and career, adding unwanted scrutiny when he was already dealing with other issues. While he hasn’t sworn off gambling entirely, the Hard Rock incident serves as a reminder of Vegas’s potential to amplify personal struggles in the unforgiving spotlight of celebrity.

Mike Tyson’s Infamous Ear Bite

Not all regrettable Vegas moments happen at the casino or wedding chapel. In June 1997, the MGM Grand Garden Arena hosted one of boxing’s most notorious moments when Mike Tyson bit off a piece of Evander Holyfield’s ear during their heavyweight title rematch. The shocking incident resulted in Tyson‘s disqualification, a $3 million fine, and the temporary revocation of his boxing license.

The “Bite Fight,” as it came to be known, permanently altered Tyson’s legacy and became one of the most infamous moments in sports. In subsequent years, Mike Tyson expressed remorse for his actions, attributing them to the rage and frustration that had consumed him in the heat of battle. The Vegas fight represents a low point in his career—a moment of losing control on one of the sport’s biggest stages.

While Tyson has since rehabilitated his public image and even formed a friendship with Holyfield, the ear-biting incident remains inextricably linked to his name. The Vegas fight demonstrates how the city’s bright lights and big stages can amplify a momentary lapse into a lifetime of regret.

Lindsay Lohan’s Costly Night Out

In 2007, at the height of her personal troubles, Lindsay Lohan reportedly ran up an enormous tab during a night of partying at several high-end Vegas clubs.

According to multiple sources, the actress spent upwards of $100,000 in a single evening on bottle service, gambling, and other indulgences while struggling with substance abuse issues. She later got into a hit and run in Las Vegas on another excursion fueled by substance abuse. 

The excessive expenditure came at a time when Lohan‘s career was already suffering due to her personal challenges, making the financial extravagance all the more problematic. What’s worse, photos of her partying appeared in tabloids worldwide, further damaging her reputation when she was purportedly trying to clean up her image.

Lohan later acknowledged that her Vegas escapades during this period represented some of her poorest decision-making. The incident epitomizes Vegas’s dangerous allure for celebrities already battling personal demons—the city’s atmosphere of excess and escape can exacerbate existing problems rather than provide the release being sought.

The Dark Side of Sin City

These celebrity misadventures highlight a common thread: Las Vegas, with its promise of consequence-free indulgence, often delivers precisely the opposite for those in the public eye. The city’s famous slogan—”What happens in Vegas, stays in Vegas“—rings particularly hollow for celebrities, whose every misstep is potentially captured by smartphones or security cameras.

For stars seeking escape from the pressures of fame, Vegas can seem like an ideal playground. But the city’s particular combination of alcohol, gambling, spontaneity, and round-the-clock temptation has proven to be a perfect storm for celebrity regrets. From impulsive marriages to career-damaging incidents, these cautionary tales demonstrate that Vegas’s bright lights can sometimes cast very long shadows.

Whether it’s a prince letting loose, a boxer losing control, or a pop star making an impulsive decision, these celebrities all learned the hard way that in the Instagram age, what happens in Vegas most definitely does not stay there—especially when you’re famous. Their experiences serve as reminders that even in a city built on fantasy, real-world consequences are never far behind.