5 Jay-Z
Before rapper Jay-Z became one of the most prominent artists of the current generation and built a billion-dollar net worth with his wife Beyonce, he pleaded guilty to second-degree felony assault with a deadly weapon. Jay-Z reportedly stabbed Lance "Un" Riviera, a record producer, at an album release party. Although little information about the 1999 incident is available, it was reported that the stabbing was a result of the alleged illegal distribution of Jay-Z's album, Vol. 3... Life and Times of S. Carter, prior to its official release.
4 Bruno Mars
Bruno Mars was found in the bathroom of the Hard Rock Hotel & Casino in Las Vegas, Nevada, gripping a bag of cocaine. After he'd been in the restroom for a prolonged period of time, the attendant alerted a security guard, to whom Mars handed the drugs when asked if he had any narcotics on his person. After being detained by hotel security, the singer-songwriter was booked into county jail for carrying 2.6 grams of cocaine. Although not nearly as severe as Tim Allen's charges, the possession of cocaine is still a felony, regardless of the amount.
3 Matthew Broderick
When Matthew Broderick is mentioned, his role as the mischievous (yet harmless) high school-ditching character Ferris Bueller probably comes to mind. Very few envision his reckless driving that resulted in the death of two people in Northern Ireland in 1987. Broderick only suffered a fractured leg and other minor injuries, and actress Jennifer Grey, who was with him, wasn't hurt. Matthew was charged with causing the death of 28-year-old Anne Gallagher and her 63-year old-mother, Margaret Doherty. Broderick's rented BMW hit Gallagher's car head-on.
2 Will Smith
In the days following Will Smith's 1989 Grammy for Best Rap Performance, he was arrested for assault, aggravated assault, and criminal conspiracy. Smith (then known as Fresh Prince) allegedly witnessed one of his bodyguards repeatedly assault a record promoter, which resulted in near blindness. In an interview following the incident, Smith made it very clear he had no part in fracturing the victim's eye socket. The charges were eventually dropped.
1 Matthew McConaughey
Actor Matthew McConaughey was arrested late 1999, dazed and confused by his own standards, while dancing naked and playing bongo drums in his West Austin home. Although arrested for suspicion of possession of marijuana and drug paraphernalia, McConaughey was later charged only for resisting transportation, a misdemeanor crime. The drug charges were eventually dropped because they weren't supported by the facts provided, and the actor only paid a fine for violating a local noise ordinance.