If You Can’t Do The Time, Don’t Do The Crime

Being a celebrity can get you out of a lot of things—no waiting for a reservation at that hot new restaurant, or easy access to sought-after designer clothing. But there’s one thing it can’t really get you out of: Jail time. These celebs learned the hard way that even their power and status can’t protect them from the long arm of the law.

Paul McCartney

Sorry, which Paul McCartney? The one from the Beatles? Time behind bars? It’s hard to believe, but the group was, at one time, a magnet for scandal and controversy. And one of those reasons was McCartney’s affinity for—gasp—the green stuff. 

He made it through various possession charges through his time with the band, but in 1980, after they broke up, he finally had to face the music—see what we did there?

Gorupdebesanez, CC BY-SA 3.0, Wikimedia Commons

Paul McCartney’s Time Served: 10 Days

While on tour with Wings, McCartney entered Japan with 8 ounces of weed in his luggage. He was detained and held while the authorities decided what to do with him. In the end, they sent him back home after holding him for 10 days.

Raphael Pour-Hashemi, CC BY 2.0, Wikimedia Commons

Felicity Huffman

Felicity Huffman had it all—a long tenure on the beloved show Desperate Housewives, a great family and marriage to A-lister William H Macy, and a promising future in show biz—but, of all people, she got dragged into a scandal that no one saw coming.

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Felicity Huffman’s Time Served: 10 Days

Huffman was just one of the stars named in the college admissions scandal of 2019, where she paid to have someone take the SATs in her daughter’s place to secure a higher score. She was later arrested for her part in the scheme, along with Lori Laughlin. Huffman’s sentence included 14 days behind bars, of which she served 10.

Tinseltown, Shutterstock

Sean Penn

Now, we know Sean Penn for his Oscar-bait roles in films like Milk, Mystic River, and I Am Sam—all of which landed him a nomination in the Best Actor category at the Academy Awards. But before that, he was a Hollywood bad boy, dating Madonna and regularly getting into trouble for getting physical with paparazzi—but that’s not what landed him behind bars.

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Sean Penn’s Time Served: 33 Days

In 1989, on the set of the film Colors, Penn got into an altercation with an extra working on the film and attacked him. He ultimately was charged with assault and sentenced to 60 days behind bars, of which he served 33.

Harald Krichel, CC BY-SA 3.0, Wikimedia Commons

Michelle Rodriguez

The Fast & Furious franchise star also appeared in blockbusters like Blue Crush and Resident Evil…and made headlines as a Hollywood party girl. Then she joined the cast of Lost—and like many of her cast members, seemed to have something of a problem with the traffic laws of Hawaii, where the show was filmed.

Gage Skidmore, CC BY-SA 2.0, Wikimedia Commons

Michelle Rodriguez’s Time Served: It’s Complicated

Rodriguez’s first DUI netted her 48 hours in jail. Her second, which happened while filming Lost, got her 5 days. This triggered a parole violation for the first charge, which came with a 60-day sentence, but she was released that same day for overcrowding. 

Then, in 2007, the parole violations piled up again after she failed to enroll in an alcohol education program or complete her community service hours. The result? A 180-day sentence, of which she served 18 days due to overcrowding. For those keeping count, that’s 25 days and say…a few hours.

Joe Seer, Shutterstock

Mark Wahlberg

Few people remember it now that Mark Wahlberg is in his Bible-thumping, bodybuilding era, but when he was just in his teens, he was involved in a horrific crime. At the time, Wahlberg had just dropped out of the earliest iteration of the New Kids on the Block, though his brother Donnie remained in the group. Then, he nearly destroyed his life—and did destroy someone else’s.

Eva Rinaldi, CC BY-SA 2.0, Wikimedia Commons

Mark Wahlberg’s Time Served: 45 Days

At just 14 and 16, Wahlberg was behind two racially-motivated attacks: the first, at 14, against Black children and later, at 16, against two Vietnamese-American men. He was sentenced to three months in jail but only served 45 days. Later, he applied for a pardon, but rescinded the application after an uproar from the public.

Michael Mattes, Shutterstock

Khloe Kardashian

We all know the Kardashians—whether we like it or not. In 2007, Khloe was arrested for a DUI, and violated her probation conditions some time afterward. That’s when she finally had to face the music and was sentenced to 30 days behind bars, and was required to enter a treatment program after her release. Only…that’s not exactly how it worked out.

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Khloe Kardashian’s Time Served: 3 Hours

After a drive to the facility—all filmed for Keeping Up With the Kardashians, of course—Khloe turned herself in. Well, she was in for a surprise. Kardashian ended up being released three hours later thanks to overcrowding. And as for the loyal Kardashian viewers? They got the unforgettable line: “Stop taking selfies, Kim. Your sister is going to jail”.

Eugene Powers, Shutterstock

Martha Stewart

It all seems like a far-off dream now, but before her “cool,” friends-with-Snoop-Dogg era, Martha Stewart was the very picture of a buttoned-up, perfectly poised upper-middle-class housewife. Her media empire began with cookbooks then expanded to TV and her namesake magazine. Then, in 2004, it all came crashing down.

Gage Skidmore, CC BY-SA 2.0, Wikimedia Commons

Martha Stewart’s Time Served: 5 Months

After being exposed as part of an insider trading scandal in 2003, she was convicted of four counts of obstruction of justice and lying to investigators. She ultimately served five months in a facility in West Virginia, and was able to spend her time engaging in hobbies that perfectly fit her “It’s a good thing” catchphrase, like ceramics and crocheting.

Peter Duhon, CC BY 2.0, Wikimedia Commons

Teresa Giudice

When Real Housewives of New Jersey first made its debut, some of its cast made veiled references to mob connections. And others, like Teresa Giudice, just shopped and shopped and shopped—paying in cash, of course. It was all extremely suspect, and eventually, investigators caught on that something wasn’t right.

Gage Skidmore, CC BY-SA 2.0, Wikimedia Commons

Teresa Giudice’s Time Served: 13 Months

Giudice and her husband Joe ended up at the center of a slew of indictments on charges of conspiracy to commit mail fraud, wire fraud, bank fraud, and making false statements on loan applications. She was sentenced to 15 months behind bars and ultimately served 13.

Sam Aronov, Shutterstock

Christian Slater

Before his defining recent role in Mr Robot, Christian Slater was equal parts 90s heartthrob and bad boy, with roles in films like Pump Up the Volume and Heathers. Unfortunately, he sometimes took that bad boy part too seriously.

Gage Skidmore, CC BY-SA 3.0, Wikimedia Commons

Christian Slater’s Time Served: 69 Days

Blame the car-centric culture of LA…or actually, maybe blame the celebs who get behind the wheel themselves. In 1989, Slater was arrested for a DUI and served 10 days. So where did we get the number 69 from? Well, in 1997, Slater was detained following an altercation with his then-girlfriend. He was given a three-month sentence, but was released after 59 days for good behavior.

Siebbi, CC BY 3.0, Wikimedia Commons

Mike “The Situation” Sorrentino

In 2009, Jersey Shore first debuted on MTV…and the world was never the same. Mike “The Situation” Sorrentino was one of the most popular—and well-paid—stars to break out of the show, but eventually, some poor decisions caught up with him.

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Mike Sorrentino’s Time Served: 8 Months

The Situation was raking it in, making bank from MTV pay checks and endorsement and appearance fees. Unfortunately, the one thing he wasn’t doing was keeping up with his taxes. Sorrentino was charged with tax fraud and tax evasion, ultimately pleading down to an 8-month sentence, which he served in 2019.

Kathy Hutchins, Shutterstock

Danny Trejo

Watch Danny Trejo in any action movie or thriller and tell me it’s not surprising that the man has a tragic—and checkered—past. But before he was a Hollywood mainstay, making appearances in fare ranging from Spy Kids to Machete, he was a troubled kid on the wrong side of the law.

Gage Skidmore, CC BY-SA 2.0, Wikimedia Commons

Danny Trejo’s Time Served: Somewhere Between 8 And 13 Years

Trejo first began selling illicit substances at the age of 7 before his first arrest at age 10. He spent years in and out of juvie before moving up to the big leagues, spending time in, as he claims, “San Quentin, Folsom, Soledad, Vacaville, Susanville, Sierra". He met Charles Manson briefly in the LA County Jail and got into boxing at San Quentin. He got sober and was released in 1969.

Ultimately, it’s hard to say exactly how much time he spent behind bars, but there’s evidence of, at minimum, a 3-year stint in juvie and 5 years out of a 10-year sentence as an adult.

Jason McELweenie, CC BY 2.0, Wikimedia Commons

Chris Brown

Chris Brown was one of the most popular R&B singers of his generation—but everything changed in one night following an altercation with then-girlfriend Rihanna which left the pop star hospitalized. Though it might be the most infamous part of his career trajectory, it’s not what landed him behind bars.

Shas Smith Photography, CC BY-SA 4.0, Wikimedia Commons

Chris Brown’s Time Served: 36 Hours

After assaulting a fan he refused to take a photo with, Brown was detained and spent 36 hours behind bars in a DC correctional facility. He was released and then ordered to report to his parole officer within 48 hours.

DFree, Shutterstock

Zsa Zsa Gabor

No one embodied Old Hollywood glamor like Zsa Zsa Gabor. Zsa Zsa and her sister Eva were even something like proto-Kardashians—beauty queens and socialites-turned celebs. Zsa Zsa made a name for herself in film…and in elite social circles, hobnobbing with A-listers and millionaires alike.

Studio publicity still, Wikimedia Commons

Zsa Zsa Gabor’s Time Served: 3 Days

But with all that beauty and glamour also came one heck of an attitude. In 1989, an officer stopped her for a traffic violation, and she ended up slapping him. She was found guilty of not only the slap, but also of driving without a license and driving with an open container (a flask of Jack Daniel’s).  

Ultimately, she was sentenced to a fine, community service, and three days in jail—which she likely would’ve gotten out of had she not refused to do the community service. And so, the Queen of Glamour spent three days in the slammer.

Walter McBride, Getty Images

50 Cent

50 Cent, AKA Curtis Jackson, began as one of Eminem’s proteges but quickly broke out as a star in his own right. He has had countless hits on the charts both as a solo artist and leader of G-Unit—not to mention all his business ventures. But before all that, he got in BIG trouble…all while still in his teens.

Senior Airman Nia Jacobs, Wikimedia Commons

50 Cent’s Time Served: 6 Months

Growing up in Queens after the death of his mother, Jackson began selling illicit substances at the age of 12. When he was 19, he was caught trying to sell to an undercover officer, and faced a sentence of 3 to 9 years behind bars. That’s when Jackson got lucky. He was able to have his sentence reduced to six months in boot camp, where he earned his GED.

The dramatic turn also inspired his name, 50 Cent—AKA change, like his ability to change his life after everything he’d gone through.

Alyssa Rose Tomfohrde, CC BY 2.0, Wikimedia Commons

Wesley Snipes

Wesley Snipes had THE career to envy in the 1990s, starting off with unexpected hits like White Men Can’t Jump and Demolition Man, culminating with his casting in the hotly anticipated Blade adaptation in 1998. And then, it unraveled—in the most unusual way.

Gage Skidmore, CC BY-SA 2.0, Wikimedia Commons

Wesley Snipes’ Time Served: 28 Months

Snipes was charged with, in short terms, conspiracy to commit tax fraud, and a tangled story unfolded involving tax protestor theory and Snipes’ claims he was a “non-resident alien” of the US, despite being born there. Ultimately he was found guilty of failing to file tax returns. He was sentenced to 3 years, ultimately serving 28 months in total.

Georges Biard, CC BY-SA 3.0, Wikimedia Commons

Paris Hilton

Were you really a starlet in the 2000s if you didn’t get a few DUIs under your belt? For a time, they seemed like a status symbol—until the consequences came to roost and people like Paris Hilton had to face the music.

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Paris Hilton’s Time Served: 19 Days

Hilton was sentenced to 45 days behind bars for probation violations stemming from various traffic charges. She showed up for her sentence at Century Regional Detention Facility in 2007 trailed by the paps. A few days in, she was resentenced to serve it at home due to an unspecified medical issue, which caused a huge uproar when the original judge in her trial found out and sent her back to jail. 

Hilton was reported to have shouted “It’s not right” in the courtroom. Ultimately, she served 19 days behind bars, some of that in a medical wing of the facility.

Kathy Hutchins, Shutterstock

OJ Simpson

We of course know OJ Simpson from the infamous murder of his ex-wife, the white Bronco chase, and the ensuing trial, which lasted months and was breathlessly covered on TV—but ultimately, that’s not what he went to jail for.

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OJ Simpson’s Time Served: 9 Years

Though he was acquitted in his big trial, Simpson was convicted of robbery and kidnapping for his role in a robbery at a hotel in Las Vegas. Ultimately, he was sentenced to 33 years with a possibility of parole after 9, which is exactly what he served, getting paroled as a result of good behavior while behind bars.

LAPD, Wikimedia Commons

Ja Rule

What’s Ja Rule better known for—his string of hits in the early 2000s, or his involvement in the disastrous Fyre Fest? Though his collaborator on that project, Billy McFarland, ended up behind bars, it wasn’t Fyre Fest that got Ja Rule in trouble.

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Ja Rule’s Time Served: 2 Years

In 2010, Ja Rule was arrested for possession of a firearm—and that’s when things got complicated. While he was already behind bars, he was also convicted for failing to pay income taxes on his earnings. He went from state to federal prison after serving his first sentence, and was released in May of 2013, after serving almost two years for the combined charges.

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Dustin Diamond

Dustin Diamond is better known as Screech from Saved by the Bell—but his career after the teen show was anything but PG. Diamond got into his fair share of scandals and legal trouble before his untimely death, but it was one run-in with the law in 2014 that put him behind bars.

BigBrother Junkie, Flickr

Dustin Diamond’s Time Served: 3 Months

In 2014, Diamond got into an altercation in a Wisconsin bar and allegedly pulled out a switchblade. One man walked away from the fight with stab wounds. A few months later, Diamond received a conviction for carrying a concealed weapon and disorderly conduct, which came with a three-month sentence.

Rob DiCaterino, Flickr

Tim Allen

Before he was the wholesome sitcom dad we grew up with on Home Improvement—or his conservative turn in Last Man Standing—Allen was up to some, ahem, less than conservative pastimes. Way back in the 1970s, Allen was a trafficker of illicit substances.

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Tim Allen’s Time Served: 2 Years, 4 Months

In 1978, Allen was detained at the Kalamazoo/Battle Creek International Airport with over 650 grams of illicit substances. Ultimately, he chose to snitch on other dealers he’d worked with in exchange for a lighter sentence. Though he was given 3-7 years, he served 2 years and 4 months before he was paroled.

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