Celebrity Arrests You Totally Forgot Happened

From afar, Hollywood appears to be a glamorous, PR-sanitized utopia. As we get closer, it is easy enough to see through the veneer of perfection that hides the often complicated mess that celebrity lives are. From courtroom sagas to jail terms, all sorts of legal troubles have tailed high-profile actors and pop culture icons the world loves. And while their privilege has frequently allowed them to go scot-free for violations that might have attracted bigger consequences for nonentities like ourselves, their arrest records are proof that fame and fortune do not place anyone above the law. 

In a twisted way, celebrity arrests have often added to the myth of stardom — right from cementing the likes of Sean Penn and Kiefer Sutherland as Hollywood bad boys to accelerating the spectacles surrounding Paris Hilton and Khloé Kardashian's lives. But it's possible that time may have faded these once front-page headlines from public memory. So here's a refresher of some celebrity arrests you probably forgot happened. 

With many cult films and a few Oscar nominations under her belt, Winona Ryder had become a defining face of '90s Hollywood stardom. So for her to be arrested in 2001, on shoplifting charges of all things, was beyond imagination. She had apparently picked up more than $5,000 worth of designer goods from Saks Fifth Avenue in Beverly Hills, setting in motion months of courtroom drama, tabloid gossip, and allegations that threatened to topple her film legacy. Both behavioral experts and nonexperts analyzed why an A-list star would need to steal. 

"If you look at what Ryder was doing to those clothes — cutting holes in them to get the tags off — do you think she was going to wear them?" Dr. Marcus Goldman, who authored a book on kleptomania, told Time. Ryder's trial was an outright media circus, with her every move and appearance subjected to intense scrutiny. In 2012, she was convicted of felony grand theft and vandalism but was acquitted of the burglary charge. Years later, she suggested to Esquire that the context of her infamous arrest was rooted more in absent-mindedness than anything else: "[T]here's so much lore around that story, but it really couldn't have been more of me thinking I'm going to my car to get something." 

Never one to play by convention, Matthew McConaughey got into trouble with the law in 1999 over the most outlandish situation, as only he could. In the wee hours of the morning on one fateful day, Austin police came knocking on his door after receiving a noise complaint. There, they witnessed a scene that could well have been straight out of an avant-garde McConaughey film — the actor was dancing naked around his house, playing bongo drums. The police reportedly found drug paraphernalia, too. 

As famous as the star of "Dazed and Confused" and "A Time to Kill" was by then, McConaughey could not evade arrest — though he did try to resist it, for which he was charged. He made it out soon after on $1,000 bail and was able to reflect on the incident in later years. At the 2024 Texas Book Festival, he recalled the advice his mother, rather unsurprised by his shenanigans, gave him at the time (via People): "You go outside in front of that media and you hold your head high." 

The year was 2010. Bruno Mars was building credibility as pop music's next big thing, with his Grammy-winning, smash hit debut album "Doo-Wops & Hooligans" — and then came an abrupt hitch on his road to fame. Mars was arrested in Las Vegas after being found with a bag of cocaine at the Hard Rock Hotel. A hotel attendant reportedly tipped off security, and upon being apprehended, the singer famously told the police that he had never used drugs before. 

Mars, who was 24 at the time, was charged with drug possession and faced a potentially damaging uphill legal battle. However, he managed to secure a plea deal that let him off a sentence on the conditions of a 12-month probation period, community service, counseling, and a fine. While this hiccup in Mars' early rise to fame eventually faded from public memory, the singer reflected in a GQ interview about the reality check it gave him: "You've slaved away for years and years and years. ... You're a kid experiencing life in f***ing Sin City, and that was the lesson: It can all be taken away. Put you in a weird place. Embarrass you." 

When Hugh Grant was arrested in 1995, he was fresh off the fame of "Four Weddings and a Funeral," the rom-com classic that set the tone for his public image as a heartthrob. So it was hardly surprising that it became a tabloid spectacle, especially considering the circumstances surrounding the case. The actor was reportedly found in a compromising situation in his car with a sex worker on the Sunset Strip. Both parties were arrested on account of "lewd conduct," and Grant's name gave the scandal front-page status. As the Los Angeles Times quoted one tabloid editor as saying at the time: "We're playing it big. ... It's an absolute shock. He's Britain's nice guy."

It didn't help that at the time, Grant was in a high-profile relationship with Elizabeth Hurley and on the precipice of a new film release. Interestingly, he didn't exactly flounder in the face of his so-called sex scandal that brought everything into question. He moved with a seemingly confident stance through the mud, quickly issuing a public apology and appearing on Jay Leno's talk show to acknowledge the episode in full: "I think you know in life pretty much what's a good thing to do and what's a bad thing, and I did a bad thing" (via YouTube). 

Tim Allen may have endeared himself to generations of fans with fuzzy Christmas films and a wholesome dad-next-door image. But the legendary actor's police record tells a wilder story. In 1978, long before he charmed audiences in "Home Improvement" and "The Santa Clause," Allen was arrested in a drug trafficking case. He was apprehended at an airport in Michigan with over 650 grams of cocaine, which could have translated into a decades-long jail term for the comedian, who was then just in his 20s. 

Allen managed to strike a plea deal and gave up the names of other dealers, securing a reduced sentence of just about two years. "It was the first time ever I did what I was told and played the game. I learned literally how to live day by day. And I learned how to shut up," he said during a podcast appearance on "WTF With Marc Maron," recalling his time in prison. "Eventually, after eight months, I got used to it." Upon his release, Allen worked his way out of his troubled past and by the 1990s, had become a household name. He landed in hot water once more in 1997 when he was booked for driving under the influence.

The curious case of Reese Witherspoon's arrest was equal parts shocking and (strangely) humanizing. Long celebrated as America's Sweetheart — a status that expects an unreasonably flawless record and a perpetually sunny demeanor from those who have it — Witherspoon went off-script in 2013 in a way that was unexpected. She was in the car with her husband, Jim Toth, when the two were pulled over in Atlanta under suspicion of drunk driving. During Toth's arrest, Witherspoon didn't just exit the vehicle against police orders but also doubled down on them. 

"Do you know my name? You're about to find out who I am," she told the arresting officers, according to dashcam footage that went viral at the time. She was arrested for disorderly conduct and later pleaded no contest, emerging from the potentially damaging situation with a clean criminal record and a small fine. Her swift public apology also helped soften the blow to her polished image: "I clearly had one drink too many and I am deeply embarrassed about the things I said. It was definitely a scary situation and I was frightened for my husband, but that is no excuse" (via The Guardian). 

Shailene Woodley's career as an activist has been inspiring but hardly smooth. In 2016, the "Big Little Lies" star was detained while protesting the controversial Dakota Access pipeline in North Dakota. It was a project environmental activists everywhere were opposing, arguing that it could potentially endanger Indigenous land and water sources. Woodley was one of 27 people apprehended at the protest site, and she live‑streamed her arrest to thousands of people online, drawing widespread attention to the incident.

"[T]hey grabbed me by my jacket and they said that I was not allowed to continue. ... And they had giant guns and batons and zip ties and they're not letting me go," she said in her broadcast, claiming that she was detained despite cooperating with authorities because of her celebrity status (via Time). Woodley managed to avoid a sentence, making her way out of Morton County Jail on a plea deal and one year of probation. In a candid recollection for Marie Claire U.K., the actor-activist talked about the toll the incident took on her: "I was strip-searched. Like get naked, turn over, spread your butt cheeks, bend over. ... You are a caged animal." 

In the 1990s and early aughts, Russell Crowe was known for more than just his superior acting chops. Over multiple years and incidents, the "Gladiator" star had earned himself a reputation as a hot-blooded young man with a notorious temper. It culminated most memorably in an altercation he was involved in at the Mercer Hotel in New York back in 2005. The episode — which has since lodged itself in pop culture history as the phone-throwing incident — had resulted in police arresting Crowe for reportedly lobbing a telephone at one of the hotel's staff members. 

The scuffle occurred early in the morning, after an annoyed Crowe had unsuccessfully tried to call his wife in Australia. The employee suffered some injuries and was treated at a nearby hospital, while Crowe was handcuffed and eventually charged with second-degree assault (among other offenses). Through the frenzied media interest in his court appearance and eventual release, Crowe maintained a stoic front but later doubled down on his apology over the incident. "I'm in a lot of trouble. I'll do my best to solve the situation in an honorable way. I'm very sorry for my actions," he told the Daily Telegraph at the time (via Australian Broadcasting Corporation).

Paris Hilton was once the It-girl at the center of it all: tabloid frenzies, 2000s pop culture, reality TV glamour. The hard-partying Y2K lifestyle she symbolized was key to her personal brand and kept fans endlessly intrigued. But beyond the glittering facade of it all, the law soon caught up to Hilton. It began with an arrest in 2006, when the Hilton heiress was found driving under the influence in Hollywood — the first in a line of driving-related violations she accumulated over the next few months. 

A year later, she was handed a sentence of 45 days, and while she didn't spend the entirety of it behind bars, the episode got enough attention to become a raging media spectacle. "It's a learning experience I'm going to grow from," Hilton told TV personality Ryan Seacrest in a famous phone chat from jail (via E! Online). "I'm so much more grateful for everything that I have, even just to have a pillow at night or food or anything." After serving a total of 23 days, Hilton walked out of jail, but it was hardly the end of her troubles. In 2010, Hilton was arrested again on suspicion of possessing cocaine. 

Those who stood witness to Sean Penn's early career in acting might remember that his off-screen antics made nearly as many headlines as his film roles. A bona fide Hollywood bad boy in the 1980s and '90s, Penn had accrued wide notoriety for his fiery temper, which often came out on sets and before the paparazzi. One such outburst that ended with the "Milk" actor's arrest came about in 1987 when, while filming the crime film "Colors," Penn punched an extra on set. As the Los Angeles Times reported, Penn had taken issue with the man clicking pictures of him and turned violent, injuring him in the process. 

At the time, Penn was already on probation for a prior assault case from 1985. For the "Colors" debacle and a subsequent reckless driving charge, he received a 60-day sentence, of which he served about half. Years later, the world learned just how far Penn's rebel streak really went. According to the biography "Sean Penn: His Life and Times," which the actor was interviewed for, he was once arrested in Macao in the '80s for attempted murder after he dangled a shutterbug from his hotel balcony (per South China Morning Post). He apparently managed to break out of jail and escape to Hong Kong.  

From financial problems to meme-famous run-ins with the media, Justin Bieber's recent transformation has sparked concern among fans trying to make sense of his public behavior. Looking closely at the pop star's timeline shows, however, that cracks had begun to appear as far back as 2014, when he was arrested for drunk driving. Bieber had been racing a Lamborghini on a residential street in Miami before he was pulled over by cops. According to Police Chief Raymond Martinez, the then-19-year-old singer was under the influence of alcohol, marijuana, and prescription drugs and initially refused to cooperate with authorities (via CNN). 

Driving with an expired license and resisting arrest also added to Bieber's list of offenses. He was released shortly after on a $2,500 bond, leaving behind a trail of press photos — including an unforgettable smiling mugshot — that recorded his arrest for posterity. While it was only the beginning of Bieber's years-long spiral into controversy, the incident was a definitive moment in the pop star's troubled story. As he reflected in a 2021 Instagram post: "Not proud of where I was at in my life. I was hurting, unhappy, confused, angry, mislead, misunderstood and angry at god." 

The transformation of Robert Downey Jr. has been stunning, to say the least. The actor may now be at the heart of a billion-dollar superhero franchise as Iron Man, but there was a time when he was one of Hollywood's most notorious cautionary tales. The troubled story of Downey's drug-addled childhood is well documented and foreshadowed a string of arrests and relapses that would plague his early fame. Throughout the '90s, the "Oppenheimer" star had multiple run-ins with the law over drug-related cases, including a momentous one in 1996 when he was found with heroin, cocaine, and a gun. 

Downey had already been in and out of jail before he received a serious blow in 1999; he was handed a three-year sentence for repeatedly violating probation tied to earlier drug arrests. "This is a person who is suffering from a disease he can't control," his attorney had argued in court (via CBS News). He served over a year of his sentence, later recalling his dire situation on "Armchair Expert With Dax Shepard": "The closest thing I can associate it to is being sent to a distant planet where there is no way home until the planets align." 

At just about three hours, Khloe Kardashian's stint in jail was a blink-and-you-miss-it affair. But given the pop culture legacy it has attained, not least because it was endlessly milked on "Keeping Up With the Kardashians," it is a moment that's etched deep into public memory. The socialite was arrested in early 2007 for drunk driving, but the case pretty much flew under the radar at the time because the Kardashians' reality show hadn't yet launched. Just as public interest in her family grew over the next year, Kardashian reportedly violated the terms of her probation and was sent to jail. 

Kardashian was originally sentenced to 30 days behind bars but was in and out in no time, owing to a dramatic twist in the proceedings. As 6ABC reported, Kardashian's arrival at the Los Angeles jail coincided with an unrelated bomb hoax and overcrowding at the facility, which led to her swift release. Notwithstanding the seriousness of the charges against her, the footage of Kardashian's pre-jail glam routine and the iconic reactions of her family members — from Kim Kardashian's selfie-taking to Kris Jenner's momager panic — turned the incident into reality TV gold.

Kiefer Sutherland belongs to that crop of Hollywood rebels who were raising hell long before the advent of tabloid gossip. But in 2007, he had to reckon with his bad boy image rather publicly when he was arrested for drunk driving in Los Angeles. This was hardly Sutherland's first run-in with the law; in fact, he was on probation for a previous DUI incident when this case imploded. The "Flatliners" actor had made an illegal U-turn, after which he was pulled over and failed a sobriety test. He was released on a $25,000 bail but was later handed a sentence after pleading no contest to the charges against him in court. 

Then the headlining star of the successful thriller series "24," Sutherland bided his time at Glendale City Jail for 48 days. In an interview with The Telegraph, Sutherland reflected on his ordeals in jail and emerged with a fresh perspective from the episode: "It was helpful in the sense that I don't ever want to go back. I am also smarter than that, and I don't want to be that guy." While Sutherland's record hasn't exactly been clean since his 2007 arrest, he has managed to stay out of prison.