14 Celebrities You Didn't Know Went To Jail

In January of 1980, Paul McCartney was arrested at customs in the Tokyo airport for attempting to smuggle a half pound of marijuana into the country. McCartney was one of the biggest rock stars in the world — but he was still breaking the law. As a result of his nine-day prison sentence, McCartney had to cancel 11 Wings concerts and pay 1 million British pounds in compensation as a result. That said, if Paul McCartney weren't a Beatle, an offense of this magnitude could have resulted in seven years hard labor.
Being a celebrity got McCartney off the hook, more or less. But fame generally doesn't matter much in the face of the law.
For a variety of reasons, these celebrities have spent significant time in prison. Some went to prison before their careers took off. Others, much like Judy King in Orange Is the New Black, were already famous. Between shifts in the kitchen at a California state prison, for example, Robert Downey Jr. regularly spoke to a Vanity Fair reporter for a profile.
Here's a roundup of celebrities you didn't know went to jail.
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Mike "The Situation" Sorrentino

On October 5, 2018, Sorrentino of Jersey Shore fame was sentenced to eight months in prison for tax evasion.
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Bill Cosby

On September 25, 2018, Bill Cosby was found guilty on three counts of felony sexual assault and sentenced to three to ten years in prison. Cosby will serve his sentence in the Montgomery County Courthouse outside of Philadelphia.

This is a significant moment in the #MeToo movement. Cosby is the first celebrity to be tried and convicted of sexual assault since the allegations against Harvey Weinstein were released in October 2017.
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Lauryn Hill

In 2016, Hill was convicted of failing to pay $1 million in taxes over the course of a decade, and was sentenced to three months in prison. Hill didn't waste any time getting back to her career. The night before she was released, Hill dropped the single "Consumerism," a song condemning corporate greed.
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Martha Stewart

At the age of 63, Stewart was convicted of insider trading — essentially, Stewart sold a company's stock based on information not yet available to the public. As a result of her selling ImClone stock just before its price plunged, Stewart spent five months at the Alderson Federal Prison Camp in West Virginia.
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Danny Trejo

This on-screen tough guy has quite a history. He was first arrested at the age of 15, and by the time he was 23, he was sentenced to San Quentin for selling heroin to an undercover cop. Between the years of 1961 to 1972, he spent time in California's Folsom, Soledad, and San Quentin state prisons.

How did Trejo go from incarceration to an acting career with over 300 credits? Trejo can pinpoint his life's turning point. In 1968, he and some friends started a prison riot, and Trejo severely injured a guard. Trejo was convinced he would be handed the death penalty, given his prior records. But since there wasn't a witness to the crime, Trejo was sent to solitary instead. A year later, Trejo was released from prison and got clean.
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Robert Downey, Jr.

Between the years 1996 to 2001, Downey was arrested numerous times for drug-related offenses. The repercussions of his crimes reached a head in 1999, when the actor was sentenced to three years in prison.

Vanity Fair wrote a long, detailed profile of the star's yearlong prison stint while he was there. In the article, the reporter asked Downey which was worse: state prison, or the L.A. County Men's Central Jail, where he spent 113 days between 1997 and 1998.

Downey responded, “That’s like asking a cellist if they prefer speed metal to acid rock, because I love both facilities equally, and I admire their tandem homage to torture.”

In 2003, Downey got sober. "I swear to God. I am not my story," he told Vanity Fair in 2014.
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Christian Slater

In 1990, a 20-year-old Slater was caught drunk driving, and sentenced to 10 days in jail. Seven years later, he spent three months in prison for assaulting his girlfriend and a police officer while high on cocaine.
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Mark Wahlberg

At the the age of 16, Wahlberg spewed racist language and assaulted two Vietnamese men with a stick, blinding one.

Though Wahlberg was a minor, he as tried as an adult for attempted murder. Ultimately, Wahlberg pleaded guilty to assault. He was sentenced to two years at Suffolk County Deer Island House of Correction, and was let out after only 45 days.
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Tim Allen

Before he was a friendly movie Santa, Tim Allen was a drug trafficker — or, at least, an aspiring drug trafficker. In 1978, a 25-year-old Allen was arrested at the Kalamazoo-Battle Creek International Airport for cocaine possession. By providing authorities with the names of other dealers, Allen avoided a possible sentence of life imprisonment. He got out of prison two and a half years later.

"It put me in a position of great humility, and I was able to make amends to friends and family and refocus my life on setting and achieving goals," Allen told Closer of his time in prison.
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Paul McCartney

In 1980, McCartney was caught at Tokyo's Narita International Airport customs with a half-pound of marijuana.

“When the fellow pulled it out of the suitcase, he looked more embarrassed than me,” McCartney said. “I think he just wanted to put it back in and forget the whole thing, you know, but there it was.”

McCartney spent nine days in the Tokyo Narcotics Detention Center, though a crime of this magnitude could've resulted in a potential seven-year prison sentence.
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Lil' Kim

In 2001, Lil' Kim was witness to a shootout that took place between her entourage and a rival group outside a Manhattan radio station. When Lil' Kim testified on behalf of her manager, Damion Butler, she lied to the grand jury. In 2005, she was convicted of perjury and sentenced to a year in prison.
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Sean Penn

In 1987, Sean Penn served 33 days in the Los Angeles County jail for attacking a film extra for the movie Colors. The extra, Jeffrie Klein, had tried to take a photo of Penn.
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Michelle Rodriguez

In 2008, Michelle Rodriguez was sentenced to 180 days in prison for failing to adhere to probation from previous drunken driving cases. Essentially, Rodriguez didn't complete her community service hours, and drank alcohol while wearing a monitoring device.

She served 18 days and was released early due to prison overcrowding.
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Ja Rule

The rapper spent two years in New York state prison for illegal gun possession, and for failing to pay approximately $1 million in taxes. He was released in 2013.

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