Trejo spent ten years, from 1959 to 1969, in and out of jail for various illegal substance-related charges. Before he entered the acting world, he launched a landscaping company after leaving the inner walls of the prison. He became a legend because of his performances in Spy Kids, Con Air, Heat, and From Dusk Until Dawn.

After a series of illegal substance possession and other charges, in 1999, Robert Downey Jr. missed a drug test and was sentenced to three years in jail. Luckily, he only served one year and was released. After these misfortunes, Downey Jr. changed his life and got some popular characters to play, including the career-changing Iron Man.

Paul McCartney wasn't famous enough to charm the Japanese authorities. McCartney was detained in 1980 at Tokyo's Narita International Airport for trying to enter the nation with half a pound of an illegal substance. To the authorities, nine days were enough to teach McCarney, and they set him free.

Martha Stewart, the famous television personality, was once arrested for a federal crime. In 2003, the US government indicted her on an outstanding nine charges of insider trading. She was a model prisoner and even earned a nickname — M Diddy. After prison, she began to rebuild her empire and even worked with Snoop Dogg for that much-needed marketing.

Oscar Pistorius, one of the most well-known athletes in the world and a double amputee, attracted the attention of his fans when he got detained for the homicide of his girlfriend, Reeva Steenkamp. Initially given a five-year sentence, the courts changed it to a longer 13 years and five months term.

Before becoming a rap legend with the release of his first album, 50 Cent was quite a troublemaker in his younger days. In 1994, 50 Cent got arrested for possessing illegal substances and a weapon. After serving six months in jail, he started his new life with a new nickname — 50 Cent.

After one night of naked bongos, the Texan Matthew McConaughey discovered himself in a prison cell. In 1999, police got called to his residence, where they found a naked McConaughey, high on illegal substances. His one night spent in jail only built his legendary icon status and helped give meaning to his saying — alright, alright, alright.

At age 16, he assaulted two Vietnamese Americans while yelling racial epithets. For this, Wahlberg was given a two-year sentence but only served 45 days. Four years later, Wahlberg shattered his neighbor's jaw in an assault, and the case got settled out of court. He changed his ways over time and became quite a star.

A$AP Rocky was imprisoned for a month in a Swedish jail in the summer of 2019 as authorities looked into his involvement in a fight with a guy on the streets in Stockholm. Despite the claims that he was protecting himself, Rocky was found guilty of assault. Luckily for him, he didn't get any additional jail time.

Michelle Rodriguez initially got a 60-day jail term for breaking her probation in 2006, but she only stayed behind bars for four hours and 20 minutes. The actress broke her probation once more a year later. She later admitted to abusing alcohol while donning a monitoring bracelet at least three times and failed to finish her community service.

Tim Allen was taken into custody on October 2, 1978, with 1.43 ounces of illegal substances on him. Allen gave up his dealers to avoid a life sentence, and following a brief stint in jail, Allen turned to comedy and didn't look back. His flourishing career shows that he made the right decision.

Member of the Hilton family, Paris Hilton used to be a headache for law enforcement. It all began in 2006 with a DUI arrest. Then, Paris Hilton ignored the license suspension and served a 45-day term in the Lynwood Detention Center before being let out if she promised to behave correctly.

Lil Wayne, also known as Dwayne Michael Carter Jr., was initially detained in July 2007 for possessing a firearm. Wayne first entered a not-guilty plea but changed his stance to guilty in return for a shorter sentence. The rapper was in prison on New York City's Rikers Island for eight months.

Charlie Sheen was detained on Christmas Day in 2009 following a fight with his ex-wife Brooke Mueller. He was jailed for the remainder of the holiday on charges of second-degree assault, threatening, and criminal mischief after being arrested in an Aspen prison. Charlie eventually entered a plea of guilty to a misdemeanor third-degree assault charge.

It’s hard to talk about celebrities and jail without mentioning Sean Penn. While he didn’t do anything huge, he was known for being extremely hostile towards co-stars and paparazzi photographers. On the set of his movie Colors, Sean Penn hit an extra. He was on probation at the time. He received a 60-day sentence, of which he served only 33 days.

A person that is hard to forget, Abby Lee Miller was given a 366-day prison term for trying to hide $775,000 in television revenue in the Chapter 11 bankruptcy case. To avoid a long sentence in prison, she pleaded guilty. In prison, she took the time to prove her health, lose 100 pounds, and found the time for studies too.

After the success of the American Pie movies, Chris Klein struggled not only with finding the next big part but also with the courts. In 2010, Chris Klein was arrested and jailed for four days for drunk driving. He was previously guilty of the same thing in 2005. After these two incidents, it seems like he has fixed his life for the best.

Boy George, a member of Culture Club, was imprisoned for four months when the Norwegian male escort Audun Carlsen was attacked and imprisoned in the singer's London apartment in 2007. He was found guilty of using excessive force and had to spend 90 days under house arrest.

Mike Tyson might have the ultimate redemption arc. After being sent to jail for multiple reasons, Tyson served only three years of his six-year sentence. After appearing in a few boxing matches and going bankrupt, he started a podcast, opened a business, and lives happily now, making more money than he did while boxing.

The former child actor frequently got detained for driving while intoxicated and having a variety of illegal substances in her possession. Although Lohan battled addiction and repeatedly checked herself into rehab over the years, she tried hard to restart her career, even signing up to work with Netflix.

Wesley Snipes filed fictitious claims for tax refunds between 1996 and 1997. From 1999 through 2004, he also failed to submit a tax return. He tried to battle the charges, citing that he was a "non-resident alien." In 2008, Snipes was sentenced to jail for three years by the United States government. 

Felicity Huffman, an actress, was detained for her involvement in an admissions conspiracy in which parents paid millions of dollars in fees to get their children into the top schools. She only served 250 community service hours, paid a $35,000 fine, and spent two weeks in jail. Her husband, William H. Macy, avoided charges for undisclosed reasons.

Son of Donald Sutherland, Kiefer Sutherland, spent 48 days in jail in 2007 after entering a no-contest plea to DUI charges and breaking the conditions of his probation. He was required to complete an 18-month-long alcohol education course and attend weekly counseling sessions after his release.

Lori Loughlin and her husband were accused of fraud and bribery in March 2019. While she declined to own up to the accusations at first, she would ultimately admit to the charges of conspiracy to conduct wire fraud and mail fraud on May 22, 2020, and would subsequently get a two-month jail term.

Jamie Waylett was a troublemaker not only in Harry Potter but also in real life. Waylett, known as Crabbe in the movies, was arrested in 2009 for growing some illegal substances in the home belonging to his family. While he was saved from jail this time, he was again arrested for participating in the 2011 England riots and had to spend two years in prison.

In 1994, O.J. Simpson, a famous football player, was accused of committing homicide against his ex-wife and Ron Goldman, her partner. Even though Simpson dodged the conviction, his public image got destroyed. Simpson received a 33-year jail term after being found guilty of attempted robbery in 2007.

James Brown and the police engaged in a fast-paced chase on Interstate 20. He was ultimately detained and found guilty of possessing an unauthorized firearm and attacking a police officer, on top of many illegal substances and driving-related charges he already had. He was given a six-year prison term but only served two. Brown managed to maintain his following base.

In the 1990s, Flavor Flav served two terms in prison. The first occurred in 1991 when he admitted to abusing his now-former girlfriend, Karen Ross. Flav continued to develop a crippling addiction, and then in 1993, after firing at a neighbor, he was sentenced to 90 days in prison for attempted homicide. Luckily, following his discharge, he started down the path of sobriety.

J. R. Smith had to deal not only with the courts of basketball but also with the ones with lawyers and prosecutors. In 2007, Smith was involved in an accident where he and two other passengers were seriously wounded. He was charged with dangerous driving in 2009 after he was found innocent of vehicular manslaughter. He served 24 days in jail.

If you ever saw The Wire, you might remember the character “Snoop” and the actress who brought it to life as one of the greatest female villains ever — Felicia Pearson. Before her role, Pearson had a troubled past. In 1996, due to her committing homicide, Pearson was sentenced to almost seven years in prison.

The 2008 arrest of Khloé Kardashian is remembered more so for Kim's selfie-taking response to learning that her sister had been jailed. Yet, given that the California jail was overcrowded, Khloé Kardashian only spent three hours of her thirty-day sentence there. Her crime? She broke probation after her DUI arrest.

Often regarded as one of the greatest rappers in history, Lauryn Hill had her dealings with law enforcement agencies. In 2012, Hill was charged with tax fraud, as she was earning royalties from movies and music. After paying a lot of money and serving three months in prison, Hill released a new song — Consumerism.

Despite having great musical talent, Phil Spector couldn't charm the criminal system. Spector shot Lana Clarkson, an actress, in the mouth and claimed that it was an accident. Spector was convicted of second-degree homicide in a 2008 retrial after the first trial resulted in a mistrial in 2007.

According to some sources, Chris Brown is commonly held as the “King of R&B.” Sadly, this reputation got tarnished by the actions he knowingly did against his then-girlfriend, Rihanna. In 2013, Brown received a 131-day jail term for breaking the terms of his probation after attacking Rihanna in 2009.

Lillo Brancato Jr. might have portrayed some junior-level criminals in The Sopranos and A Bronx Tale, but in 2005, he got arrested for an actual crime. While robbing an apartment in the Bronx, he was involved in the homicide of an NYPD officer. His crime partner got a life sentence, while Brancato Jr. was sentenced to ten years. 

It seems like Richard Hatch learned that money from victory is still a victim to the taxman. In 2011, a court sentenced Hatch to nine months in prison after determining that he had failed to pay taxes on his prize. Sadly, Hatch had already served three years in jail for tax evasion from 2006 to 2009.

After a confrontation with a server at an Atlanta nightclub on Halloween 2007, rapper Da Brat punched her with a bottle of rum. Brat was sentenced to three years in jail, seven years on probation, plus 200 hours of community service after entering a guilty plea to felony aggravated assault.

Before becoming a subject of the mini-series Pam & Tommy, Tommy Lee was already a subject of many controversies. Husband of Pamela Anderson, the star of Baywatch, Lee attacked his wife, which got him arrested. He had to serve six months in county jail. After his release, Lee and Pamela divorced, mainly due to custody issues.

A television reality star from 16 and Pregnant, Amber Portwood, has been in legal disputes for quite a long time. She was arrested for possessing illegal substances in 2011 but got released after serving a year in jail for good behavior. Sadly, she again got arrested in 2019 for domestic battery against her partner.

Ja Rule is not a stranger to some controversial crimes. In 2007, Ja Rule was arrested and sentenced for possessing illegal substances and a lethal weapon (not the movie). In 2010, Ja Rule got sentenced for attempting to get a gun. In 2011, while serving in prison, he was charged by the taxman for tax evasion between 2004 and 2006.

Clifford Joseph Harris Jr., a winner of three Grammy statues, might have released 11 studio albums in his lifetime, some of which dominated the US Billboard 200 chart — this didn’t prevent him from being arrested and charged by the federal powers. In 2009, Harris Jr. got detained due to federal weapon charges and had to serve six months in prison.

Guidice and her ex-husband Joe accepted a plea agreement that included 41 charges of fraud, and as a result, she got sentenced to a 15-month jail term. The reality star turned herself into the authorities at FCI Danbury in January 2015 to begin her 15-month sentence, and she was freed on December 23, 2015, just after 13 months.

Joe Giudice was found guilty of fraud in October 2014 and received a sentence of 41 months in prison. In March 2016, he was required to check into a New Jersey prison. In 2018, the courts decided to deport Giudice after the sentence. Guidice spent months fighting his deportation, but it all was in vain.

A court sentenced Meek Mill to between two and four years in jail in November 2017 for violating the conditions of his probation after his arrest in 2007 on multiple charges when he was 19 years old. Before being granted early release in April 2018 by a Pennsylvania appeals court, the rapper completed five months of the sentence.

After his plea to charges of driving while intoxicated from a DUI incident in June 2010, Vince Neil was placed on lockdown at the Clark County Detention Center in Las Vegas for ten days in 2011. Before that, he was imprisoned for 20 days in 1986 for vehicular manslaughter and drunk driving.

After shooting his cousin, Rick was found guilty of attempted homicide in 1991. He received a three to ten-year sentence but only served five. He came dangerously close to being deported as a foreigner who had spent more than five years inside an American prison. But, after successfully winning a lawsuit, he was allowed to reside in New York.

Lil Kim went to prison for a year for fabricating some information about a shooting her friend was in. For lying to a federal grand jury, Kim was found guilty in 2005 on three conspiracy charges and perjury. She spent a year at the Philadelphia Federal Prison Center and another 30 days in house detention.

The True Romance actor was initially detained for drunk driving in 1989 and jailed for ten days. Slater was arrested again in 1997 for attacking his fiancée and a law enforcement officer while under the influence. After being found guilty, he served three months in prison before completing three months of rehabilitation.

In 2007, Remy Ma entrusted her friend with her handbag. After Ma got it back, she thought she was $3000 short and thus assaulted her friend. Sadly, a gun went off, which hit the friend in the abdomen. While she claimed it was accidental, the jury didn’t believe her and sentenced her to eight years. She only served six years.

While nobody can beat Kim Kardashian popularity-wise, Mike Sorrentino came close. With earnings reportedly topping $5 million in 2014, he forgot to pay some of it that rightfully belonged to the government. In 2019, Sorrentino entered a New York correctional facility and was allowed to leave after serving eight months.