5 actors who have served time in prison

In a harrowing series of events, That '70s Show star Danny Masterson has been sentenced to 30 years to life in prison on two counts of ra*e. He had reportedly invited the victims to his home, drugged them, and had his way with them while they were vulnerable. The conviction came on September 7, 2023, from the Los Angeles Court after he was accused of ra*e on three instances.

While this is not the first time that Hollywood stars have been sentenced to serve time in prison, this is undoubtedly one of the most disturbing cases of recent times. However, the fact that the victims have received justice, even after almost two decades, instills hope in the judiciary system.

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With Masterson's case in the headlines, we went through a shockingly long list of Hollywood actors who went to prison and have brought up some of the biggest names on it. In this article, we list out the most notable A-listers who had to serve time in prison.

Mark Wahlberg, RDJ, and three other big actors who have been to prison

1) Mark Wahlberg

Mark Wahlberg is undoubtedly one of the most prominent actors in Hollywood when it comes to action, comedy, or even drama. With a career spanning over 30 years, Wahlberg has been a household name for his work in Boogie Nights (1997), The Italian Job (2003), Ted (2012), and other critically and commercially successful films.

Although he has made a name for himself in the acting industry, Wahlberg has had a rocky past. In 1986 and 1988, at ages 15 and 16, he was involved in instances of racial violence and assault. He received a civil rights injunction for the 1986 incident but was sentenced to serve three months in prison for felony assault.

Wahlberg served 45 days before being released. He was again involved in a case of assault in 1992 when he, along with one of his buddies, assaulted his neighbor Robert Crahn. However, the case was settled outside of court.

2) Robert Downey Jr.

Robert Downey Jr. is arguably one of Hollywood's most successful and talented actors. The actor started his career early in the 1980s and racked up critical acclaim for his work in theater and 80s films. The following decade, between the 90s and 2000s, was also a great time for Downey as an artist.

However, he ran into multiple legal troubles in 1996. With a father who was a drug addict, Downey had also developed an addiction to substances from an early age. He got arrested multiple times on various drug-related charges and was charged with probation.

However, after missing multiple compulsory drug tests, Downey was sentenced to three years at the California Substance Abuse Treatment Facility and State Prison in 1999. He spent nearly a year in prison before being released on a $5,000 bail. Although he ran into more trouble until 2004, Downey did not have to serve any more time.

3) Sean Penn

Sean Penn is an internationally acclaimed actor and director with multiple Academy Awards. However, alongside an incredibly decorated career spanning over 40 years, Penn has also had numerous run-ins with the law.

Sean Penn was arrested three times between 1985-86 for cases of assault and battery on paparazzi, journalists, and one time on singer-songwriter David Wolinski. All of these were somehow related to Madonna, his girlfriend at the time.

However, in 1987, Penn was arrested and sentenced to 60 days in prison for punching an extra on the set of Colors (1988). He was released after spending six days in jail for a previous film commitment and later served more time at the Los Angeles County Central Jail. He ended up serving only 33 days of his 60-day sentence.

4) Martha Stewart

Although not a mainstream actor like the other names on this list, Martha Stewart made her fair share of fame and stardom that can even challenge some of the most popular stars. Similarly, her legal trouble was slightly different from others on this list.

In 2001, Martha Stewart got involved in a high-profile insider trading case at the biopharmaceutical company ImClone Systems Incorporated. She was accused of having insider information coming from her broker at Meryll Lynch, Peter Bacanovic. Based on that, she sold all of her shares in the company and avoided a loss of $45,673, according to the SEC.

She went to trial in 2004 on charges of securities fraud, obstruction of justice, and others. Stewart was found guilty on multiple charges and sentenced to serve five months at the Alderson Federal Prison Camp.

5) Tim Allen

Tim Allen rose to fame with his role in the 90s ABC sitcom Home Improvement. Starting as a comedian in the late 1970s, Allen steadily built up his popularity in the local circuit of Detroit before moving to TV gigs.

Even before his career could blow up, Tim Allen got caught in 1978 at the Kalamazoo Battle Creek International Airport in Michigan with over 1.4lb of cocaine in possession. He was arrested and charged with drug trafficking and was set to get sentenced to life in prison. However, he pleaded guilty to the charges and offered to disclose the details of his associates for a reduced sentence.

For his cooperation, Allen received a sentence of three to four years in prison, of which he ultimately had to serve only two years and four months before being released on parole. In 1998, he was arrested again for DUI but only received a year of probation and necessary alcohol abuse rehabilitation.

While all of these actors have served time in prison, none seem as inhumane as Danny Masterson's case. None of them received such a severe sentence as Masterson did of life in prison. Our heart goes out to the victims and their families.