In 1978, Tim Allen was arrested at the Kalamazoo/Battle Creek International Airport in Michigan for possession of cocaine. He pleaded guilty to drug trafficking and spent two years and four months in prison in Minnesota.
Mark Wahlberg served 45 days of a three-month sentence in jail when he was 16 for assaulting two Vietnamese men while attempting to rob a convenience store with a metal stick. He said he was “high” when it happened.
Robert Downey Jr.
Robert Downey Jr. went to prison multiple times for drug possession between 1996 and 2001. In 1999, he failed to show up to a court-ordered drug test, so he was sentenced to three years in a substance abuse facility/prison in California run by the state. A judge released him after serving 12 months.
In 2005, Lil’ Kim was sentenced to one year and one day in prison, for three counts of perjury and one account of conspiracy. She was released in 2006.
In 2013, Lauryn Hill was sentenced to three months in prison because she allegedly didn’t pay taxes on $1 million in income. She served the full three months in a facility in Connecticut and was released in October 2013.
In 2004, Martha Stewart was sentenced for insider trading and went to a federal women’s prison in Alderson, West Virginia. Stewart served five months in prison, five months of house arrest, and two years of probation.
In 1994, O.J. Simpson was acquitted in the slayings of his ex-wife, Nicole Brown Simpson, and her friend, Ronald Goldman. On December 5, 2008, Simpson was sentenced to 33 years in prison with eligibility for parole in nine years (in October 2017). On July 20, 2017, Simpson was granted parole and was freed on October 1, 2017.
In 1998, Tommy Lee served 6 months in prison for battering his then-wife, actress Pamela Anderson.
In 2008, actor Wesley Snipes was sentenced to 3 years in prison for failure to file tax returns from 1994 to 2000. He began serving the sentence in 2010 and was released in 2013.
In 1992, Tyson was convicted on one count of rape and two counts of deviate sexual conduct against Miss Black America contestant Desiree Washington on July 18th, 1991 and sentenced to six years in prison, but was released on parole after serving three years.