1. Tim Allen

Before achieving acting success and fame in the television sitcom Home Improvement and movies such as the Toy Story and The Santa Clause franchises, Tim Allen worked as a comedian before his arrest on federal drug trafficking charges.

After serving over two years in prison, Allen resumed his standup career. In 1998, he was sentenced to Probation for driving under the influence (DUI).

2. Justin Bieber

In 2014, pop singer Justin Bieber had multiple brushes with the law. He was arrested in Florida for suspected DUI and resisting arrest. He pleaded guilty to lesser charges. He served two years of probation for vandalizing his neighbor’s house in California. He was also charged with reckless driving and assault resulting from a traffic accident in Canada. The singer has stayed out of trouble and married model Hailey Baldwin in 2018.

3. Robert Downey Jr.

The Iron Man star struggled with drug addiction for years. His 1996 arrest for possessing drugs and a firearm was the first of several run-ins with the law through 2001. After prison and serving probation, Downey went into rehab and has since been clean and sober.

4. Eminem

Famed Detroit rapper Eminem received a year of probation after his 2000 arrest for carrying a concealed weapon and firearm offenses. A charge of assault from a separate case was dropped as part of a guilty plea for the first two charges.

5. Felicity Huffman

The college admissions cheating scandal in which affluent parents paid thousands of dollars to ensure their children’s acceptance to the nation’s most elite colleges and universities caught up a few celebrities, including actress Felicity Huffman of Desperate Housewives. She pleaded guilty to paying $15,000 for someone to take the Scholastic Aptitude Test (SAT) in her daughter’s place to increase her score fraudulently. Huffman served two weeks in prison.

6. Khloe Kardashian

Reality tv star Khloe Kardashian faced DUI charges before becoming a household name in Keeping Up With the Kardashians. She was sentenced to three years of probation after her 2007 arrest.

7. Natasha Lyonne

The Poker Face and Orange is the New Black actress had some brushes with the law in the early 2000s. She was initially charged with DUI in 2001; three years later, she was accused of harassing a neighbor, trespassing, and mischief. Lyonne was jailed overnight for missing a court date for the 2004 complaint against her.

8. Sean Penn

The notoriously prickly actor earned a reputation for physically confronting media members. He pleaded no contest to assaulting two journalists in 1985, was charged with two more assaults in 1986, and spent more than a month in jail in 1987 for assault and reckless driving. In 2010, Penn was sentenced to community service and anger management therapy for an incident with a photographer.

9. Winona Ryder

The star of Beetlejuice and Girl, Interrupted, was surprisingly arrested in 2001 for stealing $5,500 in items from the upscale Saks Fifth Avenue department store in Beverly Hills, California. After her convictions for shoplifting and grand theft, Ryder was sentenced to probation and community service and had to pay fines and restitution. She has since found success, most recently in the Netflix series Stranger Things.

10. Martha Stewart

The lifestyle entrepreneur was convicted of securities fraud and obstruction of justice in 2004. Stewart used insider information to sell her shares in ImClone before their value dropped. She served five months in prison before being released and has since seen her business interests expand and prosper.

11. Tiger Woods

The golfing legend stunned the world with his 2017 DUI arrest after he was found asleep behind the wheel of his car in a traffic lane during the middle of the night. He pleaded guilty to lesser charges, paid a fine, and received community service and probation.

12. Jay Z

Rap superstar Jay Z faced serious charges after stabbing music producer Lance “Un” Rivera in a nightclub in 1999 over a dispute about the rapper’s albums being sold as bootlegged copies. Jay Z reached an agreement with prosecutors, pleading guilty to third-degree assault in exchange for three years of probation.