20 Male Celebrities Who Have Spent Time Behind Bars (2)

Tim Allen

This one might come as a shock to most people. Tim Allen spent two years in prison after he was caught in Kalamazoo, Michigan, with almost two pounds of cocaine. He was also involved in drug trafficking

Ja Rule

Ja Rule is another celebrity who tried to avoid paying taxes and was also in possession of an illegal firearm. He spent two months and four days in jail.

Danny Trejo

Danny Trejo’s career has transformed into a very successful one, but before he was the star we know today, the actor spent 11 years in jail for drug and robbery charges.

Wiz Khalifa

Can you guess what this rapper was arrested for? Khalifa was arrested and jailed for trying to sneak marijuana onto an airplane. Shocking.

Chris Brown

The young rapper has had trouble with the law for years. He eventually got what was coming to him when he was convicted in the Rihanna domestic abuse case. Brown spent 108 days behind bars.

Lil Wayne

The infamous hip-hop artist spent five months in jail for having illegal weapons and marijuana on his tour bus. His fans started a social media movement to release the artist before his sentence was complete.

Paul McCartney

One of the surviving Beetles stars spent 10 days in jail after he was caught in an airport with half a pound of marijuana.

Wesley Snipes

Wesley Snipes spent three years in prison after another case of tax evasion. He was recently released and has returned to the movie industry.

Robert Downey Jr.

It’s hard to imagine that Robert Downey Jr. has a dramatic history involving drugs and legal issues, but the actor spent one year in jail for trespassing and drug charges. He’s one of the few celebrities to clean up his image and stand as a role model for many people.

Kiefer Sutherland

“24” star Kiefer Sutherland may be an American hero on the television show, but the actor spent 48 days in jail after he was arrested multiple times for driving under the influence.