Celebs Who Have Done A Lot Of Jail Time

The news cycle includes a steady rotation of celebs who've done something or other to warrant their arrest. DUIs, drug charges, and domestic spats are just grist for the tabloid mill. Usually these crimes just result in a memorable mug shot and a tough week or two for said star's PR team. And then there are the celebs who spent ridiculously short periods of time in the slammer, including Lindsay Lohan (82 minutes) and Nicole Ritchie (84 minutes), according to Prison Legal News. And let's not forget Paris Hilton, who was released on day three of her 45-day sentence due to an "undisclosed medical condition," per the Los Angeles Times.

The list of instances of legal leniency for A-Listers is long, however, there are some famous faces who've had to pay a much bigger price for their much more serious misdeeds. Read on to see who served a significant chunk of time behind bars. 

Home Improvement star Tim Allen needed life improvement back in the '70s, when he was busted on some serious felony drug charges. According to CBS News, In October 1978, Allen got caught at the Kalamazoo/Battle Creek International Airport in Michigan in possession of about a pound and a half of cocaine. He entered a guilty plea to a charge of drug trafficking, and facing a life sentence, he worked out a deal with prosecutors: three to seven years in prison in exchange for providing the names of other drug dealers with whom he associated. Of that reduced term, Allen served two years and four months in a Minnesota prison before getting paroled, at which point he turned things around by getting into comedy (which proved quite the successful move).

The experience was obviously life-altering for Allen. "It put me in a position of great humility," he told Closer Weekly, "and I was able to make amends to friends and family and refocus my life on setting and achieving goals."

Richard Hatch is best known as the (sometimes nude) winner of the first season of Survivor. Unfortunately for him, the million dollar prize ended up becoming something of a burden, as Hatch was sent to jail for nine months in 2011 when a judge found him guilty of not paying taxes on his winnings. 

That sentence was on top of the three years Hatch had already spent in prison for tax evasion between 2006 and 2009. According to Forbes, he survived a total of 51 months in the big house on charges of not only tax evasion, but also for "violating prison media-access rules" when he did an NBC interview shortly after his second release from prison. This resulted in a third incarceration, which included solitary confinement. Exactly how did Hatch violate those rules? "The Bureau of Prisons has argued that the permission was for one interviewer, not three," which Hatch disputed, claiming "the permission allowed him to be interviewed by NBC, not a specific interviewer."

If that all sounds complicated, that's because it is. But you know the simple way to not get on the feds' radar in the first place? Pay your taxes.

On Halloween 2007, rapper Da Brat reportedly got into a heated argument with a waitress at an Atlanta, Ga. nightclub and hit her in the face with a bottle of rum. Da Brat (real name Shawntae Harris) pled guilty to felony aggravated assault and was sentenced to three years in prison, seven years of probation, and 200 hours of community service. She served the time, and then in 2014, a judge ruled that she also had to pay the victim (who sustained permanent scarring to her face) $6.4 million.

Later speaking with BDO about her incarceration, the "Give It 2 U" rapper said, "I think God does everything for a reason and it was meant for me to sit down and regroup and think things over and realize I shouldn't take anything for granted. I have to be very careful about my actions and what I say to people and how I react. I think I am a better person, a wiser person, a smarter person who is not going to take anything for granted anymore."

Former heavyweight champion boxer Mike Tyson is, in a word, terrifying. On top of erratic and violent behavior both in and out of the ring, he has also spent a significant amount of time in prison.

In March 1992, Tyson was convicted of rape, and received a six-year sentence (and, notably, the support of future U.S. president Donald Trump). He ended up serving three years, which, if his autobiography Undisputed Truth is, indeed, indisputable, were fairly non-punitive. In the book, the boxer claims he started a consensual relationship with a female drug counselor and was having "so much sex that [he] was too tired to even to go the gym and work out... [he'd] just stay in my cell all day." 

Tyson has stayed out of prison and kept his nose clean, converting to Islam and starting up a career in entertainment with the cartoon series The Mike Tyson Mysteries and a memorable cameo in The Hangover. However, the conditions of his parole did require him to join a registry of sex offenders.

Charles S. Dutton has had quite a long and prolific acting career, appearing in film and TV since 1985. Prior to that, "Roc" also had quite the prolific criminal life. According to the Los Angeles Times, Dutton served hard time stemming from sentences for manslaughter, illegal possession of a firearm, and acting as the ringleader of a prison riot.

That all sounds bad, particularly the manslaughter part, but Dutton explained that it all stemmed from his troubled upbringing in the rough part of Baltimore. "I quit school in the seventh grade. I thought there was more happening on the corner. In my neighborhood ... you were expected to go to prison. It was a given, like some kids expect to go to college," he told the Los Angeles Times, adding, "I've never done anything I've been ashamed of. I never hurt anybody who wasn't trying to hurt me. But I was wrongheaded, that's for sure." He explained that the manslaughter charge was from a fight in which he defended himself after being "stabbed seven times." His opponent ended up dead.

But Dutton says he "adapted" to his close to 10 years of "prison life," rather than allowing himself to be "conditioned by it." On the inside, he found theater, which led to his true calling, and after his parole, he really turned things around, eventually graduating from the Yale School of Drama. 

The Godfather of Soul, Mr. Dynamite, the hardest working man in show business—regardless of how you know and remember the late singer today, James Brown was once known as inmate No. 155413 at South Carolina's State Park Correctional Center, where he served three years out of a six-year sentence for brandishing a gun at an insurance company and then leading cops on a car chase in 1987. According to The New York Times, Brown was found guilty of carrying a deadly weapon at a public gathering, attempting to flee a police officer, and driving under the influence of drugs

He got out in 1991, but alas, Brown apparently couldn't help himself and essentially reenacted his original crime. According to Time, he led police on another car chase in South Carolina after discharging a rifle at his home in 1998. This time, Brown managed to avoid round two in the slammer; he was sentenced to a drug rehabilitation program instead.

Oh, and that classic mugshot above? That was from an arrest for domestic violence, when he was accused of pushing his wife to the floor. He spent an overnight in jail for that one and was released the next day, eventually pleading no contest to the charge and paying a fine as punishment. 

Chuck Berry virtually invented rock and roll in the 1950s, providing a blueprint for the frenetic, electric guitar-and-R&B-derived genre still followed by performers today. Berry recorded one stone-cold, undeniable classic after another, like "Maybellene," "Roll Over Beethoven," and "Johnny B. Goode." Berry parlayed some of the money he earned racking up early rock n' roll hits and tirelessly touring into a St. Louis nightclub.

According to J.P. Robinson's "The Trial of Chuck Berry," while at a bar in Juarez, Mexico, in 1959, he met a 14-year-old girl named Janice Escalanti, and he offered her a job working the hatcheck booth at his club. Escalanti was fired three weeks into the new job, upon which she went to the St. Louis police and alleged that throughout the long trip from Juarez to the Midwest, and then at his home, Berry had assaulted her as many as 14 times.

In March 1960, a jury convicted Berry of violating the Mann Act, a law from 1910 that banned the transportation of a woman across state lines "for the purpose of prostitution or debauchery." After earning a five-year sentence, an appeals court ordered a new trial, owing to racist comments made by the judge in the first trial. The conviction was upheld, and Berry ultimately served two years in prison. Prior to his prison stint in the 60s, according to Robinson, Berry also "served three years in prison" for an armed robbery conviction when he was 18 years old.

Hip-hop has historically been a male-dominated industry, with less than 10 women rapping in a #1 hit on the Billboard pop chart, per ABC News. One of the first was Remy Ma (real name: Reminisce Smith), who, as a member of Fat Joe's collective Terror Squad, topped the charts in 2004 with "Lean Back." In 2006, Remy Ma released her solo debut There's Something About Remy: Based on a True Story, but her rising stardom would be interrupted by a serious criminal matter.

In July 2007, according to The New York Times, Smith and her friend, Makeda Barnes Joseph, went to a birthday party at a nightclub in New York's trendy meatpacking district, and during the festivities, Smith asked Joseph to hold her purse. When Remy Ma got her handbag back, she believed it to be suddenly short of $3,000 in cash. Later that evening, Smith confronted Joseph in her car, jumping into the latter's vehicle with a cocked and loaded gun and trying to take Joseph's purse to look for that missing cash. The two women fought over the bag, and in the struggle, Smith's gun went off and fired a bullet into Joseph's abdomen. Smith then drove off in her Cadillac Escalade before abandoning it in favor of a taxi. Smith attested that the shot was accidental, but a jury wasn't convinced, convicting the rapper of "intentional assault." Per MTV, Remy Ma earned an eight-year prison sentence, but she was released in 2014 after serving six.

After debuting with the Notorious B.I.G.'s Junior M.A.F.I.A., Lil' Kim struck out on her own with her double-platinum solo debut Hard Core, and spitting provocative, sexually-charged verses on smash hit, high-profile collaborations in the late '90s and early 2000s, including "Crush on You" (with Jay-Z), "Not Tonight" (with Da Brat and Missy Elliott), and "Lady Marmalade" (with Christina Aguilera and Pink).

In February 2001, New York radio station Hot 97 was the site of a shootout, for which Lil' Kim was reportedly present, according to MTV. When police questioned the rapper, she claimed to have no idea why shots were fired that day, which police believe originated over a feud between Lil' Kim and Foxy Brown — the two rappers' entourages exchanged heated words before guns went off.

Lil' Kim was ultimately indicted and convicted on one count of conspiracy and three counts of perjury for lying to authorities. She told a federal grand jury that her co-manager Damion Butler wasn't present during the incident... although he later confessed to taking shots at the rival group, per MTV. She also told a court she couldn't identify a photo of another man allegedly involved in the shooting, but that guy turned out to be Suif "Gutta" Jackson, a member of Junior M.A.F.I.A. Lil' Kim was sentenced to 366 days in prison, but was released after serving about nine months in the Philadelphia Federal Detention Center.