10 Most Hilarious Crimes in Celebrity History

By Kelsey Allen

Celebrities are known for their looks, wealth, homes, vacations and of course talent. But with all of the money and access comes a darker side that some celebs have a hard time avoiding. From drunk shopping escapades to quick affairs with prostitutes, these are some of the most hilarious crimes in celebrity history.

  1. Shia LaBeouf: Before Shia LaBeouf was arrested for drunk driving in the summer of 2008, he had a less dangerous, more humorous altercation at a Walgreens in Chicago. In November 2007, the Transformers star headed to a Walgreens store for pimple cream and cigarettes, after a night of drinking. After his first trip to the store, however, the intoxicated LaBeouf realized that he had forgotten the cigarettes, so he changed clothes (as part of a disguise) and returned to the store. He bought gummy bears but again forgot to buy cigarettes. LaBeouf went back to Walgreens a third time, wearing a new hoodie, and told the clerk "Well, buddy, it’s your worst nightmare" after the clerk teased him for changing so many times. Ultimately, LaBeouf was arrested for trespassing and refusing to leave the store, but the case was dropped.
  2. Charles Barkley: Rushing to the hospital is a common excuse for speeders who are caught by the police, but Charles Barkley revealed a little too much of the truth when he was pulled over for passing a stop sign. The basketball player and sports commentator told the police officer that he was in a rush because he was hurrying to drive around the corner and get a blow job. The police officer also notes that Barkley told him that the same woman who accompanied him had given him a blow job "one week earlier," and said "it was the best one [Barkley] had ever had in his life." That night, Barkley was arrested for drunk driving.
  3. Hugh Grant: British actor Hugh Grant is still considered a romantic comedy star and an A-list celebrity, but in 1995 he was famously arrested for misdemeanor lewd conduct in a public place with a prostitute. The scandal occurred just before Grant’s first major film release, but instead of damaging his career, Grant’s attitude toward the arrest helped amp up his image. He surprised the industry and the public by refusing to make excuses for himself and simply stating, "I think you know in life what’s a good thing to do and what’s a bad thing, and I did a bad thing. And there you have it."
  4. Kid Rock: Musician Kid Rock has earned five Grammy nominations, but he’s also accumulated a string of arrests, mostly stemming from his feud with Tommy Lee. When Kid Rock began dating Lee’s ex-wife Pamela Anderson, he called Lee in jail to tell him the news. After a few years of almost-fights between the two musicians, Pamela Anderson divorced Kid Rock and began dating Tommy Lee again. At the 2007 MTV Video Music Awards, Tommy Lee stole Kid Rock’s seat when he went to the bathroom. When he returned, Kid Rock slapped Lee in the face and then punched him, sort of like you do in elementary school.
  5. George Michael: George Michael enjoyed a successful pop career in the 1980s and 1990s as part of the pop duo Wham! and as a solo artist. But his sexuality and public image were questioned in 1998 when he was arrested in Los Angeles as part of a sting operation that resulted in Michael’s "engaging in a lewd act" in a public restroom. The undercover police officer "started playing this game," Michael explained, "which I think is called, "I’ll show you mine, you show me yours," which ultimately resulted in his arrest.
  6. Nikki Blonsky: Long Island actress Nikki Blonsky became a became a national sweetheart when she won the role of Tracy Turnblad in the film version of Hairspray in 2007. The smiling, giggly twenty-year-old was even nominated for a Golden Globe and appeared on several talk shows to discuss her success, but in 2008, she and her father were arrested at the Providenciales International Airport in the Turks and Caicos Islands. Blonsky and her father were accused of starting a fight with America’s Next Top Model alum Bianca Golden and her family, during which Golden’s mother was injured and Golden claimed that Blonsky sat on her. Blonsky was charged with, and later cleared of, causing actual bodily harm, and her father was charged with assault and causing grievous bodily harm.
  7. Winona Ryder: Actress Winona Ryder was one of the most popular, most successful movie stars in the 1990s, appearing in films like Edward Scissorhands, Beetle Juice, Mermaids, Little Women, The Age of Innocence, and Reality Bites. When her career started to lose its spark in the late 1990s and early 2000s, Ryder made headlines for her shoplifting arrest. In December 2001, she was arrested in a Beverly Hills Saks Fifth Avenue for shoplifting $4,760 worth of items. She was charged with grand theft and for illegal possession of prescription drugs, though her attorney insisted that Ryder was not under the influence of the painkillers at the time. One year later, Ryder was sentenced to three years’ probation, 480 hours of community service, $3,700 in fines, and $6,355 in rest
  8. Eddie Murphy: Comedian and actor Eddie Murphy was a favorite on Saturday Night Live and has appeared in successful films like Beverly Hills Cop and Dreamgirls, for which he won the Screen Actors Guild for Actor in a Supporting Role. But during a gap in his career, Murphy was involved in a scandal that involved a cross-dressing prostitute. In 1997, Murphy was pulled over by police, and the prostitute was ultimately arrested on charges from another warrant.
  9. Kelly Osbourne: Kelly Osbourne stood up for her fiance’s reputation and subsequently was arrested. Zoe Griffin, a celebrity journalist from the UK publication The Mirror, allegedly "reported that Osbourne’s fiance, Luke Worrall, did not know how an earthquake occurred," according to Wikipedia. In 2008, Osbourne allegedly slapped Griffin for her comment and was arrested for assault in January 2009.
  10. Boy George: In the 1980s, Boy George was an English icon and international celebrity, famous for his unique musical style and dress code. Currently, Boy George continues to write songs and release albums, but no longer enjoys the same celebrity status. In fact, his public image has been tarnished by a recent, disturbing arrest that involved Boy George and a male escort. In 2007, Boy George, after taking cocaine, became paranoid that the escort had hacked into his computer. George handcuffed the escort to the wall and beat him "with all sorts of sex toys and chains," reports Hollyscoop. In January 2009, Boy George was sentenced to 15 months in jail.