ByElle McFarlane, writer at
'There's always someone younger and hungrier coming down the stairs after you.'
Elle McFarlane

If you're lucky, the closest you'll ever get to prison will be finding yourself stuck in relationship with a previously closeted maniac, making your livelihood predominantly using excel or, getting given the Dawson's Creek Boxset for Christmas and feeling compelled to watch it in its entirety, even though you wish nothing but pain and suffering upon all the characters with the exception of Jen (RIP).

As dark as each of these scenarios are, however, just be grateful that you can (in theory) find a way to escape their incarcerating clutches. The following celebrities were not so fortunate, but they did find a way to use their time inside to their own benefit, be it spiritually, financially or even sexually — here's looking at your Sinatra.

1. Lil Kim: Lying to a Federal Jury

Never one to miss an opportunity to bring in the dollar, in the two months leading up to her year long prison sentence, Kim worked furiously to finish her fourth album Naked Truth which was released on the day she received her sentence. It went on to sell 190,000 copies and debut at #6 on the Billboard 200 in its first week.

If that wasn't enough, Kim also filmed a reality series Countdown to Lockdown, a six-part show which followed her in her last 14 days of freedom before her incarceration, gathering 1.9 million viewers nationwide.

2. Shia LaBeouf: Trespassing, Disorderly Conduct at a Cabaret Performance and Assault

Racking up an impressively diverse list of criminal offenses including attempting to stab his neighbor, refusing to leave Walgreen's and disturbing a performance of the musical Cabaret by shouting aggressively at the on-stage actors, LaBeouf is no stranger to time behind bars.

Opening up about his experiences in the alternative prison cookbook, Prison Ramen, LaBeouf revealed however that his time inside made him reflect and, ultimately, was a cathartic experience:

"When I'm nervous in my creativity, I think of my failures in life and in art. Thinking about my screwups loosens the grip of fear. It's freeing to f--k up and to recover."

3. Martha Stewart: Insider Trading and Obstruction of Justice

After a six-week trial, Stewart was found guilty of making false statements to federal investigators about her part in an insider trading conspiracy and was duly sentenced to five months behind bars.

Although it wasn't all that bad, upon being assigned a job in floor maintenance, Stewart, in conversation with Oprah, revealed her joy at discovering a new cleaning tool — a rug cleaner, going on to say:

"I had the best time, that place was sparkling when I left.”

This coupled with that fact that her company returned to soaring profits the year after her incarceration, as well as a highly lucrative partnership with Wal-Mart and a new television series Martha Stewart's Cooking School on PBS, it's safe to say that all publicity is good publicity.

4. Michelle Rodriguez: Assault, Drink Driving, Violating Probation

Following a series of speeding, hit and run and drinking under the influence charges, the Fast and Furious star was sentenced to one hundred and eighty days in prison after violating her probation, although she only served eighteen days due to ‘overcrowding.'

Speaking to TV Guide however, Rodriguez had a rather optimistic approach to doing time for a DUI saying:

"It was so cool! [Laughs] I love people, and it was a primal crew. The only thing that keeps them going is fighting for salt and making dice out of soap. It was an amazing experience. I wouldn't take it back for anything.”

5. Jeremy Meeks (The Hot Felon): Weapons Charges & Being Criminally Sexy

Finding fame after the public went wild for his particularly sexy pouting mugshot, Jeremy Meeks has since rocketed to international stardom being referred to predominantly as the 'Hot Felon.'

Since leaving jail, Meeks has hired an L.A. based agent and signed a modeling contract. Judging by his Instagram account, he's got a strong post-prison career ahead of him.

You might also like:

6. Robert Downey Jr.: Possession Charges, Trespassing

Hollywood's most lovable bad boy Downey Jr. has been sent behind behind bars numerous times, nearly all on drug related offenses. After a particularly bad run which included five years going in and out of prison, Downey finally broke the circle of substance abuse by attending rehab.

Since leaving prison his career has sky rocketed, scoring roles in The Singing Detective, A Scanner Darkly, Kiss Kiss Bang Bang, Zodiac and Iron Man as well as starting his own production company, 'Team Downey' with his wife Susan and becoming the highest paid actor in Hollywood by 2015.

7. Frank Sinatra: Seduction and Adultery

Back in 1938 when 'seduction' was a criminal offense, Sinatra was arrested in a nightclub after one of his girlfriends attacked his wife-to-be Nancy who later had him arrested twice for his mischievous philandering.

However, his criminal past in combination with his piercing blue eyes, ties to the mafia and playboy life style only made him all the more irresistible to his legions of fans the world over, proving that he could literally do no wrong.

8. 50 Cent: Possession with Intent, Assault and Battery

Back in 1994, young aspiring rapper Curtis Jackson III was sentenced to nine years in prison on drug related charges, although he only actually served six months. Determined to make something of himself, upon his release he immediately started rapping and changed his name to 50 Cent as a metaphor for change.

After a further set back in 2000 which saw him get shot nine times, 50 ended up becoming one of the world's best selling rappers, founding G-Unit Records and selling over thirty million albums worldwide. Unfortunately in 2015, he filed for bankruptcy with a whopping thirty million dollars of debt.

But never fear, two days ago he uploaded a video of him wearing a two hundred thousand dollar golden chain. Whether he owns it or not however, is up for debate.

9. Piper Kerman: Money Laundering

Piper was sent to prison for thirteen months after entering into a whirlwind romance with a woman called Catherine Cleary Wolters, a heroine dealer, and smuggling over ten thousand dollars from Chicago to Brussels for her.

Five years later she published her memoire, Orange is the New Black: My Year in a Women's Prison, which was then promptly picked up by Jenji Kohan and transformed into an award winning Netflix show of the same name, with Taylor Schilling playing Piper and Laura Prepon playing Catherine.

She now teaches writing classes at the Marion Correctional Institution and the Ohio Reformatory for Women.

10. Akon: Not Actually Getting Locked Up

What do you think about when you think of 2004? The launch of Facebook? The untimely split of Bennifer? Or, perhaps you remember it as the year Akon released his seminal album, Trouble and the year gleefully pumped out it’s numerous hits including Lonely, Belly Dancer (Bananza), Pot of Gold and his debut single Locked Up.

Locked Up depicts Akons' three year stretch in prison after being part of an auto-theft ring between 1999 and 2002. However, The Smoking Gun challenged Akon’s claims after they failed to find court records relating to this case, stating that in fact, Akon had never even been to jail.

Talking to Access Atlanta, Akon had this to say about how the media had misinterpreted him:

"Right. So I guess when I was being interviewed, and I would say, 'Yeah I did about a good three years,' I wasn't saying I did a three-year stretch. I was calculating the time from when I started to get in trouble to the time when I said, 'Enough is enough.”


Do you think you could profit from doing time like these celebs?

(Sources: Prison Ramen; Oprah; TV Guide; The Smoking Gun; Access Atlanta)


Latest from our Creators