The pressure of stardom is high, and even celebrities like Paris Hilton and Matthew McConaughey have had a taste of the justice system more than once. From naked bongo sessions to free shopping sprees, here’s some A-Listers whose criminal records make quite the interesting read.

Lindsay Lohan

In May 2007, Lindsay Lohan had her first run-in with the law after crashing her Mercedes while under the influence of alcohol and cocaine. A second arrest soon followed, when Lindsay, 37, was apprehended in July after chasing a woman. Charged with driving with a suspended license, driving under the influence, and cocaine possession, the star served 84 minutes of her one-day sentence before being placed on three years’ probation.

In October 2009, this was extended by 12 months so Lindsay could complete court-ordered alcohol treatment – but when she missed a court date to attend the Cannes Film Festival, a judge invoked £78,000 bail and fitted the star with a drug-monitoring anklet. While at the MTV Movie Awards the following year, the drug anklet lit up and Lindsay was ordered to pay a further £163,380.

After failing to attend alcohol class in summer of 2010, Lindsay served two weeks of a 90-day jail sentence. That September, the star was sent to rehab, where she attacked a member of staff. After reaching out for help, the star said, “It is clear to me that my life has become completely unmanageable because I am addicted to alcohol and drugs.”

Nicole Richie

Nicole and her Simple Life co-star Paris Hilton, both 42, were regulars on the party scene – but in October 2002, the adopted daughter of Lionel Richie earned her first mugshot following a New York nightclub brawl.

Although charges were dropped, it wasn’t long before the socialite was arrested again. Detained for a DUI in Malibu, Nicole was sentenced to three years’ probation after driving without a valid licence and with heroin in her vehicle.

After a few trouble-free years, Nicole was pulled over in December 2006 after entering a freeway from the wrong direction. The star failed her drugs test, admitting she had taken pain medication Vicodin and smoked marijuana. The severity of the offence – and its potential for causing serious injury to others – resulted in a trial.

At the time of her court appearance, the judge sentenced Nicole – who was pregnant with her first child – to four days behind bars, three years’ probation, and fines totaling £1,616. However, due to overcrowding, she spent just 82 minutes in jail. Speaking of her remorse, Richie said, “If I could personally apologise to every single person that has lost a loved one from drunk-driving, I would.”

Paris Hilton

Socialite and heiress Paris has earned her rep as America’s ‘It’ girl, but things took a turn in September 2006, when Paris, now 42, was arrested for drink-driving. After her license was suspended, the star was given 36 months’ probation and fined just under £1,200.
In February 2007, the star was yet again stopped behind the wheel. Coupled with her lack of attendance at a court-ordered alcohol programme, the judge deemed that she should serve 45 days behind bars, with Paris screaming to the court, “It’s not fair!”

The star served only 23 days due to good behavior, but in August 2010, was arrested yet again. A Las Vegas police officer found the heiress and her then-boyfriend Cy Waits smoking marijuana and in possession of cocaine. After pleading guilty to possession of illegal drugs and obstructing an officer, the starlet received a year’s probation, 200 hours of community service and a £1,578 fine.

Matthew McConaughey

At 2.37am on 25 October 1999, police responded to a noise complaint at a residence in Austin, Texas. There, they discovered a naked Matthew McConaughey, 54, dancing around his house while playing the bongos.
Officers reported that the Oscar-winning actor was so intoxicated that he was unable to stand and that when they asked the “nude subject” for identification, McConaughey replied, “You’re violating my rights! You can’t come in my house like this!” After offering the star some clothes – which he refused – he was dragged naked into a police car, wrestling with officers.

After a search of his rented home revealed marijuana, a bong and other drug-related paraphernalia, Matthew was charged with possession of drugs and resisting transportation. The charge was later reduced to noise violation, resulting in a £40 fine. Talking to Playboy magazine, the actor insisted, “What’s wrong with beating on your drums in your birthday suit? I have no regrets.”

Robert Downey Jr

In April 1996 the actor, 58, was arrested for speeding down Sunset Boulevard while in possession of heroin, cocaine, and an unloaded gun. While on parole and under the influence of drugs, he then trespassed into a neighbor’s home. After failing to attend compulsory drugs testing while on probation for his offenses, Robert spent six months in jail.

In 1999, he yet again missed a drugs test and was sentenced to a three-year prison term at a drug treatment centre. The judge later ordered him to pay equivalent to £4,000 and granted him early release after a year.

A career resuscitation saw Robert star in legal drama Ally McBeal – but as ratings soared, police found the relapsed actor wandering the streets barefoot, under the influence of cocaine. In November 2004, he told Oprah Winfrey, “When [you’re] a wreck [and] you just lost your job, you might want to give [rehab] a shot.”

Heather Locklear

The darling of 80s and 90s prime-time TV, Dynasty’s Heather Locklear, 62, is the not-so-proud owner of three mugshots. In September 2008 the actress was pulled over on suspicion of drink driving and it was later determined anti-anxiety medication was responsible for her erratic behavior; Heather was placed on probation and given a fine. But in 2010, the star was charged with a misdemeanor after hitting a parking sign and required to attend a rehab programme for abuse of prescription medication.

In 2011 police were called to a domestic disturbance between Heather and fellow Melrose Place actor boyfriend Jack Wagner. But Heather’s latest arrest came in 2018, when police were called to her home by her brother to break up a dispute with her then-boyfriend. The domestic violence charges were dropped, but Heather faced four counts of battery relating to the police officers and was banned from owning a firearm.

Kiefer Sutherland

At the height of his 24 fame playing CIA agent Jack Bauer, Kiefer’s massive million-pound salary made him the highest-paid actor on TV, but he couldn’t seem to stay out of trouble. In 1989, the now 56-year-old was arrested for DUI and carrying a concealed, loaded weapon. In return for pleading no contest to reckless endangerment, the charges against the actor were dropped.

Then, in September 2007, he was released on £19k bail after yet another DUI arrest. In violation of his parole, the actor was ordered to serve 48 days behind bars.

And in May 2009, Kiefer handed himself in at a New York police station after allegedly headbutting fashion designer Jack McCollough at a party the evening before. At the time, reports said the incident arose after McCollough pushed actress Brooke Shields and refused to apologise. A rep for McCollough stated, “He would not hurt a fly. All we can say is that he was the victim of a violent, unprovoked assault.” Misdemeanor charges were dropped, and Kiefer apologised in a statement.

Winona Ryder

Winona was at the height of her fame when she was arrested for shoplifting in 2001. The Hollywood actress, who was 30 at the time, was observed by security guards picking up multiple designer items as she walked around Saks Fifth Avenue in Beverly Hills. She eventually purchased a leather jacket and two blouses for around £2,400, before guards challenged her about the unpaid items. She responded by asking, “Didn’t my assistant pay for them?” before later claiming she was shoplifting to prepare for an upcoming role.

A televised six-day trial ensued, and found guilty of grand theft and vandalism, the actress was placed on three years’ probation and given 480 hours of community service. In later interviews, the Stranger Things star, now 52, said her judgement was clouded by the overuse of prescription painkillers, adding, “It wasn’t what people think. It wasn’t, like, the crime of the century.”