10 Times Entitled Celebrities Went to Jail or Broke the Law

Top 10 Times Entitled Celebrities Went to Jail Broke the Law

Welcome to WatchMojo, and today we’re looking at celebrities who apparently felt they were above the law, yet would ultimately face consequences, including jail time in some cases.

Ezra Miller

Ezra Miller couldn’t slow down in 2022, igniting controversy left and right. On a trip to Hawaii, Miller racked up charges such as harassment, disorderly conduct, and second-degree assault. Miller walked away with a restraining order and a $500 fine, but they didn’t learn their lesson. Throughout the remainder of the year, Miller was accused of grooming and burglary. While Miller pleaded not guilty to the burglary charge, they pleaded guilty to a trespassing misdemeanor, receiving a year probation. Some argued that Miller got off easy, as Warner Bros. stood by “The Flash” star leading up to the film’s premiere. Between that movie’s historic financial failure and Miller’s legal troubles, though, the industry seems to be turning on them, even recasting some of their roles.

Martha Stewart

The face of a homemaking empire, Martha Stewart seemed like the last person who’d find herself behind bars. That turned out not to be the case when Stewart sold her ImClone Systems shares, sparking an illegal insider trading investigation. In 2004, Stewart was found guilty of conspiracy, obstruction of justice, and making false statements. Stewart only spent five months in prison with two years of probation, but some wondered if her reputation would recover. Yet, it wasn’t long until Stewart was back hosting TV shows, writing books, and even defining friendship goals with fellow ex-con Snoop Dogg. Whether or not Stewart’s career actually benefitted from the negative press, it’s safe to say her prison stint didn’t hurt.

Justin Timberlake

In 2007, Justin Timberlake accepted a Brit Award. During his pre-recorded speech, the pop star pleaded with a certain somebody to “stop drinking” and that they were “going to get sloppy.” While he didn’t mention anybody by name, this clip would come back to haunt Timberlake and delight Britney Spears stans 17 years later. During the early hours of June 18, 2024 in the Hamptons, Timberlake was arrested for driving while intoxicated in addition to ignoring a stop sign and not staying in his lane. Timberlake allegedly claimed that he only had “one martini,” although he refused to take a chemical test three times. Within the next day, he was being arraigned while his mugshot was made public.

Felicity Huffman & Lori Loughlin

What do Lynette from “Desperate Housewives” and Aunt Becky from “Full House” share in common? That’s right, they both have twin sons! The actresses behind these characters also have something in common: the 2019 Varsity Blues scandal. Huffman and Loughlin were among several others accused of buying their children’s way into college. In Huffman’s case, she reportedly paid someone $15,000 to take the SATs for her daughter. Huffman pleaded guilty to conspiracy, as did Loughlin. Along with fines and community service, both would do time. Huffman was sentenced to 14 days, serving only 12, while Loughlin faced a harsher punishment… of two months. Since then, Loughlin made fun of herself on “Curb Your Enthusiasm” while Huffman booked a guest spot on “Criminal Minds: Evolution.”

Lindsay Lohan

Substance use and an intrusive paparazzi didn’t help Lindsay Lohan during her darkest hours. At the end of the day, though, her actions were her own. The actress was given plenty of chances, going to rehab following one DUI arrest, only to be caught driving under the influence again shortly after. While Lohan got off with probation and the shortest of jail stints, she repeatedly failed to meet the court’s demands. For violating her probation, Lohan was ordered to spend 90 days in jail and another three months in inpatient rehab, although she only served 14 days supposedly because of overcrowding. Lohan later faced jail time for the theft of a necklace and violating probation, but overcrowding cut her stay short again and again.

Paris Hilton

Paris Hilton is another name that couldn’t stay out of the tabloids in the 2000s. In Hilton’s case, she seemed to relish the mentality that any publicity is good publicity. Hilton’s notoriety climaxed in 2006 when the LAPD caught her driving intoxicated. The heiress walked away with three years probation, a $1,500 fine, and a suspended license. Actually, we guess you could say she drove away, as Hilton got caught speeding a month later, which was just one of her probation violations. The judge threw the book at Hilton. Of course, it was a thin book with Hilton receiving 45 days in jail. 40 of those days were spent under house arrest, but Hilton seemingly learned her lesson… until her next arrest in 2010.

Jussie Smollett

With the hit show “Empire” in its fifth season, Jussie Smollett seemed to have it all. Jamal Lyon was not only seen as a breakthrough role for Smollett, but a trailblazing character for LGBTQIA+ people of color. Those who looked up to Smollett started to sing a different tune after 2019. At first, it appeared that Smollett was the target of a hate crime at the hands of two brothers. Upon further investigation, authorities deduced that Smollett orchestrated the whole thing, paying the brothers to participate in the so-called attack. While the initial charges against Smollett were thrown out, he’d soon face another indictment regarding the false report. In 2022, Smollett was sentenced to 150 days in jail, although he’s still appealing two years later.

Elizabeth Holmes

Elizabeth Holmes built herself up as the Steve Jobs of the medical world, promising to change healthcare through her company Theranos. Investors, the government, and the public wanted to believe Holmes’ blood tests were as revolutionary as she claimed. Maybe it was wishful thinking, but people were given various reasons to trust Holmes until a select few looked closer. When Theranos was revealed to be a colossal hoax, Holmes’ reputation and net worth were wiped out. Things only got worse for Holmes from there, being found guilty on four criminal fraud counts. Some were upset that Holmes wasn’t also found guilty of defrauding patients, but a form of justice had been served with the face of Theranos starting her 135-month prison sentence in May 2023.

Harvey Weinstein

The #MeToo movement has shined a spotlight on numerous big names accused of abusing their power, including Bill Cosby, Danny Masterson, and R. Kelly. Yet, no downfall shook up the industry more than Harvey Weinstein’s. For decades, Weinstein’s aggressive behavior was something of an open secret. It wasn’t until dozens of women came forward in 2017 that many realized the full extent of Weinstein’s crimes. With his list of accusers eventually exceeding 100, Weinstein would be trialed in New York and Los Angeles, being found guilty in both cases. Weinstein’s New York verdict was controversially overturned in 2024 due to “egregious errors.” A retrial has been ordered, but Weinstein is far from a free man with his 16-year LA sentence still intact.

Donald Trump

Donald Trump has faced a revolving door of court appearances since 2023, but the most prominent trial thus far concerned hush money allegedly paid to Stormy Daniels amid the 2016 election. On May 30, 2024, the former president was found guilty on all 34 counts regarding falsifying business records. This wasn’t the first time Trump lost a high-profile case, being found liable for defamation and abuse against E. Jean Carroll only a few months earlier. However, this was Trump’s first criminal conviction in federal court. What’s more, Trump became America’s first president turned felon. Trump’s pending sentence could prevent him from voting for himself in the 2024 election. No matter what punishment Trump receives (if any), it won’t stop him from running for president.

What’s the most criminal example of entitlement you’ve ever witnessed on the celebrity circuit? Let us know in the comments!