Martin Luther King Jr.

Medium / No Public Domain

Some of the folks on this list have long RAP sheets, but almost no one can touch Martin Luther King’s 29 arrests. Of course, the civil rights leader was a target for the police, like the time he was taken to jail an Alabama jail for driving 30 mph in a 25 mph zone.

If King’s arrests attest to anything, it’s that often times people who are arrested are not necessarily criminals, but are challenging societal norms. While in jail in Birmingham, Alabama, King outlined his future efforts in a now-famous letter where he wrote, “Injustice anywhere is a threat to justice everywhere.”

David Bowie

David-Bowie-Mugshot
Rochester New York Police Department / Posted by thesmokinggun.com

Musicians seem to have a very unhealthy relationship with the law, and getting arrested almost seems like a necessary skill for a rock star’s resume. David Bowie’s is a great example because people don’t remember his crime, but his mugshot has widely been considered the most attractive celebrity mugshot ever.

This photograph was almost never seen by the public, as it was recovered from a trash can in 2007 when Bowie’s estate was being settled. He was arrested in March 1976 for possession of a half-pound of marijuana and went to jail one night with Iggy Pop and another musician.

Steve McQueen

Steve-McQueen-mugshot
Anchorage, Alaska Police Department / Posted by Chris Lambos

Not to encourage anyone to copy Steve McQueen’s behavior when he was arrested, but the story lives up to how cool the late actor really was. He was arrested in Anchorage, Alaska of all places, when he drove up and down the main avenue “turning brodies” while extremely intoxicated.

The fun part came when officers asked him to perform a field sobriety test, and according to an eye witness, McQueen proceeded to do somersaults down the line. McQueen fought the charge and was able to avoid a drunk driving conviction. It’s unknown whether he’s flashing “peace,” or “victory,” but it looks like he wins!

Mike Tyson

Mike-Tyson-mugshot
Maricopa County Sheriff / Posted by thesmokinggun.com

The only man that can top MLK’s 29 arrests is former boxer, Mike Tyson. His personality has always been a little out there, but most remember the three times he was arrested after becoming “Heavy Weight Champion of the World.” You would also be surprised to learn that he was arrested 38 times by the time he was 13 years old!

The above mugshot might be arrest number 40, but we can’t say for sure. What we do know is that it involved Tyson’s lifelong addiction to narcotics. Shortly after leaving an Arizona nightclub in 2006, he almost struck a police cruiser with his BMW. A subsequent stop found that he was under the influence and in possession of the white devil powder.

Kurt Cobain

Kurt-Cobain-mugshot
Vintage Everyday / Aberdeen Police Department

The mugshot below shows a 19-year-old Kurt Cobain who was arrested in 1986 for spraying graffiti on a building. Reports have long said that he spray painted, “God is gay,” on the building, but according to a 1993 interview of the Nirvana front-man, he wrote something else entirely.

Apparently, he actual wrote, “ain’t got no how whatchamacallit,” and rumors about the “gay” comment come from the fact that in high school he befriended a gay classmate, and was subsequently bullied for it. According to one his personal journals, Cobain wrote, “I am not gay, although I wish I were, just to piss off homophobes.”

Lee Harvey Oswald

Lee-Harvey-Oswald-mugshot
Hulton Archive / Getty Images

We’ll spare you the suspense — Lee Harvey Oswald shot President Kennedy. The only question is: did he act alone?

Oswald fled the sixth floor of the Texas School Book Depository, headed home, and when he went out again he was stopped by a Dallas Police Officer. Oswald shot him four times and killed him.

Oswald ran into a movie theater and was arrested in his seat. From the moment he was handcuffed, he denied that he shot anyone. What he did or didn’t know we’ll never find out, because he was in custody for less than 48 hours before another assassin, Jack Ruby, shot him while he was being transported.

Jimi Hendrix

Jimi-Hendrix-mugshot
Metropolitan Toronto Police Department

Jimi Hendrix is widely considered the greatest guitarist that ever played. He was gone too young, but he was almost lost to Johnny Law sooner. Hendrix touch downed at the Toronto International Airport on May 3, 1969, and was arrested after authorities found hash resin and heroin in his bag.

Hendrix spent a total of four hours in jail and was given a police escort to the concert that night. He flew home, then was back in Toronto seven months later. After a three day trial, his lawyers pulled some magic and he was acquitted. Hendrix said, “Canada has given me the best Christmas present I ever had.”

Malcolm X

Malcolm-X-mugshot
Wikipedia Commons

If it’s difficult to recognize Malcolm X from his mugshot below, but that’s understandable because he went through quite the transformation in prison. In 1946, after his third arrest in two years, he was sentenced to six-and-a-half years in prison after committing a string of burglaries in the Boston area.

Upon arrival in prison X, then known as Malcolm Little, was nicknamed “Satan” by his fellow inmates because he paced around muttering bible verses. When he came out of his fog, he began devouring books like an ant on a sugar mound. He then joined the Nation of Islam and became an extremely influential leader in the civil rights movement.

Charles Ponzi

Charles-Ponzi-mugshot
The Smoking Gun

The mugshot below is of the man, the myth, the infamous legend, Charles Ponzi, the inventor of the Ponzi scheme. Ponzi arrived from Italy in the United States with just $2.50 in his pocket, and sixteen years later he would be a millionaire. It’s a bit complicated, but Ponzi developed a scheme that bilked investors of $7 million.

Ponzi’s robbing Peter to pay Paul method was foiled when a government agency said his scheme was impossible. It was also revealed that he had been arrested two previous times for fraud. Living the high-life came crashing down and on August 12, 1920, he was arrested and spent the next three-and-a-half years in prison.

Jane Fonda

Cuyahoga County Sheriff’s Office / AP Images

On November 3, 1970, actress and political activist Jane Fonda was arrested at an airport in Cleveland for possession of drugs. If she looks defiant in her mugshot, it’s for two reasons: she didn’t have drugs on her — they were vitamins, and she had been targeted by the White House because of her anti-Vietnam War efforts.

This mugshot became a symbol of defiance, notably for her raised fist and “punk-style” haircut. When authorities questioned her she got into a “tussle” with police officers. She remained defiant and was released after her arraignment the next day. She was charged with possession and assault but was acquitted of both charges.

Benito Mussolini

Benito-Mussolini-mugshot-Fascism
Rare Historical Photos

That’s Italian Dictator Benito Mussolini below, and this mugshot was taken in Bern, Switzerland almost 20 years before he became “Il Duce.” It’s surprising to note that the virtual father of Fascism was actually a devout and outspoken socialist for most of his life, and that landed him in hot water with authorities in multiple countries.

In 1903, Mussolini supported a general strike and got arrested in Switzerland. After two weeks in jail, he was deported back to Italy. He didn’t stay long, as he returned to Switzerland and was arrested again. He returned to Italy and returned to preaching socialism. Over the course of the next 20 years, he would take a radical turn right.

Bill Gates

Bill-Gates-mugshot-Microsoft
Wikipedia Commons

Bill Gates dropped out of Harvard University in 1975, moved to New Mexico, and started a new company with his friend Paul Allen — Microsoft. But if you thought the ascension of Microsoft into a Fortune 500 company was fast, you’ve never seen Bill Gates drive.

His first big splurge was in 1979 when he bought a Porsche 911. Prior to that, he had already been arrested twice for traffic violations. In the case of the above mugshot, he was caught blowing by a stop sign, as well as driving without a license. Gates got the last laugh though, as this mugshot maybe the outline for Microsoft’s Outlook People Pane.

Rosa Parks

Getty Images

Not all who are arrested are criminals, even if they are convicted. While you take a moment to ponder that thought, think about Rosa Parks refusing to give up her bus seat on Dec. 1, 1955, and her subsequent arrest two months later for violation of state segregation laws.

Four days later, African-Americans and others stopped using the bus. The Montgomery Bus Boycott raised issues with the law all the way to the Supreme Court, who ultimately ruled that the law was unjust. It also had another effect, as the young pastor who led the effort became an extremely important civil rights leader, Martin Luther King.

Jim Morrison

Jim-Morrison-mugshot-The-Doors
Flickr / Dade County

You may remember other mugshots of Jim Morrison, and the reason for that is he’s been arrested no less than six times. In this instance, it was his antics on stage that got him trouble at a Miami concert. He was charged with lewd and lascivious behavior, indecent exposure, profanity, and public drunkenness.

Emphasis should be placed on that last charge because Morrison didn’t remember much about that show. To appease the situation authorities offered to drop the charges if The Doors played a free concert in Miami9 — a request that they refused. Morrison was sentenced to six months in prison, but he died in Paris before he could serve his time. In 2010, he was given a posthumous pardon.

Pablo Escobar

Wikipedia Commons

Have you noticed how many of these guys are smiling? Bill Gates and Pablo Escobar were on Forbes billionaires list multiple times, but that’s where the similarities end. Escobar is smiling because he knows he’s not going to get in trouble for his 1976 arrest for drug trafficking.

When he was arrested, Escobar gave the officers a choice: “plata o plomo.” It means “silver or lead,” and in this case, the officers chose the lead. They refused to accept a bribe from Escobar and ended up losing their lives because of it. As for Escobar, he beat the charges and became the most successful drug dealer in the history of planet earth.

Joseph Stalin

Joseph-Stalin-Mugshot-Russia-Soviet-Union-communism
Rare Historical Photos

If you translate the information posted on Joseph Stalin’s mugshot, you’ll find out that he “looks around 32 to 34 years old,” and has ears six inches long. He was first arrested in 1908 for “revolutionary activities,” and after two years in exile, he escaped by dressing up as a woman and boarding a train.

He was arrested again in 1911, producing the above mugshot when he was involved in terrorism, robbery, and revolutionary activities, which led to him being exiled again. Stalin once said, “I trust no one, not even myself.” It’s especially relevant here because the person charged with bribing him out of prison kept the money for himself instead. Stalin then had him shot years later.

Johnny Cash

Johnny-Cash-mugshot
Michael Ochs Archives / Getty Images

Jim Morrison got arrested six times, and while that is rather impressive, consider that Johnny Cash was arrested seven times. His music would suggest that he spent a great deal of time in prison, but despite being arrested so many times, he only spent one night in jail his whole life.

But his arrests, including the one above in October 1965, for bringing a suitcase with hundreds of “pep pills” and tranquilizers after returning from Juarez, Mexico only inflated his career. Two of his most successful albums are “Johnny Cash at Folsom Prison” and “Johnny Cash at San Quentin.”

Patti Hearst

Patti-Hearst-mugshot
FBI.gov

Patti Hearst had the whole country scratching their heads, as she was first kidnapped by a domestic terrorist group in February 1974, later defaulting to their cause by April. The daughter of newspaper mogul William Randolph Hearst was caught in a bank surveillance tape brandishing an assault rifle during a robbery.

Hearst was finally captured by the FBI in September 1975, and despite the fact that she argued during her trial that she was brainwashed by her captors, the jury found her guilty. She served two years in prison after President Carter commuted her sentence (President Clinton later pardoned her).

John Dillinger

John-Dillinger-mugshot
FBI.gov

The first time John Dillinger was arrested he confessed to the crime, and was given an outrageous prison sentence. After nearly 10 years in the can, he began robbing banks immediately upon his release. He was arrested again, so his buddies used force to bust him out, and killed the sheriff in the process.

Dillinger and his gang continued marauding the country until he was arrested again in 1934. This time Dillinger busted himself out when he produced a revolver that he carved out of wood. This would be his last arrest, as law enforcement killed him on site instead of dealing with another confrontation.

Mick Jagger

Mick-Jagger-mugshot-Rolling-Stones
Brixton Police Department / The Smoking Gun

In 1967, the Rolling Stones were one of the most popular rock bands in the world when their front-man, Mick Jagger, and lead guitarist, Keith Richards, got into some trouble. A tip to police led to them raiding the home of Richards, and the two of them ended up in a Brixton jail in England.

Richards was sentenced to a year in prison for allowing people to smoke marijuana on his property, while Jagger got three months for possession of over-the-counter “pep pills” from Italy. An appeal was made as the sentences were considered very harsh, and Jagger ended up spending just one night in jail.

Lucky Luciano

Lucky-Luciano-mugshot
Wikimedia Commons

In February 1936, authorities came to the Waldorf Astoria Hotel to arrest crime syndicate leader Lucky Luciano, but he wasn’t there. Luciano had a bellboy on his payroll and was able to escape through a secret elevator, later fleeing to Arkansas after the bellboy tipped him off.

Unfortunately for Luciano, a New York police officer who was working another case saw him and recognized him on the spot. Luciano came to face 62 charges, convicted of running a prostitution ring. He obly served 10 years of his 50-year sentence, because he was released after securing an alliance between the mafia and US government during WWII.

O. J. Simpson

O.-J.-Simpson-mugshot
Los Angeles Police Department

For all that was made of Simpson’s famous “white Bronco” chase on June 17, 1994, consider that Simpson was only a fugitive for less than 10 hours. But that chase was like the moon landing — anyone with a TV was watching. Simpson was asked to surrender after being implicated in the death of his wife and her friend Ron Goldman, but he had other plans.

It’s been argued that Simpson meant to commit suicide, as he wrote a note that said, “I’ve had a great life, great friends. Please think of the real O.J. and not this lost person. Thanks for making my life special. I hope I helped yours.” Simpson would spend the next 14 months in jail before he was acquitted.

Vladimir Lenin

Vladimir-Lenin-mugshot
Flickr

Vladimir Lenin became the first Premier of the Soviet Union in 1917, but prior to that, he was a revolutionary and all-around nuisance to the Russian monarchy. He became radicalized at an early age after his brother was hanged in 1887 for plotting to assassinate Tsar Alexander II.

Lenin began organizing union members to the Marxist cause, and in December 1895, he was arrested. After a year in prison, he was exiled to Siberia for three years, then he went to Western Europe after that. Lenin returned to Russia in 1905 and spent the next dozen years galvanizing Russian workers into the Marxist fray.

Larry King

Larry-King-mugshot
Dade Country Sheriff / Reddit

At the end of Larry King’s career, he was considered one of the most trusted men in news, but the script could’ve been a lot different if things had worked out differently in 1971. In that year, he was given a sum of $5,000 to pay to another man, and instead of delivering the money, he kept it for himself.

He used the money to pay off back taxes owed, and on Dec. 20, 1971, he was arrested in Miami for grand larceny. He was effectively fired from his broadcasting job but escaped conviction because of the statute of limitations. He returned to Miami in 1978 and got his old job back, and started “The Larry King Show” later that year.

Benjamin “Bugsy” Siegal

Benjamin-“Bugsy”-Seigal-mugshot
Wikipedia

“Bugsy” Siegal was part of Lucky Luciano’s hit squad called “Murder Inc.” but despite dozens of murders that were somehow linked to him, he only was ever convicted of two crimes – gambling and vagrancy. He was arrested many times, however, including in 1928 (when this mugshot was snapped).

A fellow gangster once said of Siegal, “Bugsy never hesitated when danger threatened… When it came to action there was no one better. I’ve never known a man who had more guts.” He also absolutely hated his nickname “Bugsy,” and would go on to be tried for more crimes, including murder, but was only ever convicted of the two minor crimes.

Frank Sinatra

Frank-Sinatra-mugshot
Michael Ochs Archives / Getty Images

This mugshot was taken in Bergen, New Jersey in November 1938, and it shows a 23-year-old Frank Sinatra before he gained international fame. His charge, ahem, was brought on by the fact that he had “intercourse” with a woman of good repute.

 

It’s almost unthinkable that a person could be arrested for such proceedings, but Sinatra faced “seduction” charges nonetheless. After 16 hours in jail, he was released on bond. Three months later(January 1939), the charges were dropped after it was revealed that the woman was married. The court tried to charge him with adultery, but in the end, the case was dismissed.

Charles Manson

Charles Manson

Charles Manson was no stranger to the law when he was arrested for the last time on April 22, 1971, having already spent 16 years in prison. What’s interesting is that Manson represents a rare case, because he was convicted on seven counts of first-degree murder, but he didn’t kill anyone.

Instead, his cult of followers that were called “The Manson Family,” acted based on his specific instructions when they murdered their victims. It’s also interesting that the police didn’t catch up with Manson and his “family” because of good old fashioned investigating, as Manson was originally arrested for suspicion of auto theft.

The OG “Machine Gun” Kelly

Machine-Gun-Kelly-Mugshot
Wikipedia

George Kelly Barnes actually got his nickname “Machine Gun” Kelly from his wife. She thought it would increase his notoriety as a criminal and she was right. After being arrested a few times during prohibition for bootlegging, he and his wife Kathryn hatched a scheme to kidnap a wealthy Oklahoma oilman and demand a ransom.

They were paid their $200,000 ransom but didn’t count on their victim remembering everything about where he’d been, despite the fact that he was blindfolded. The Kelly’s fled, but were caught up with weeks later on September 26, 1933. For their crimes, they both received life sentences.

James “Whitey” Bulger

James-"Whitey"-Bulger-mugshot

Boston gangster “Whitey” Bulger was arrested in 1956 for hijacking and armed robbery, but this mugshot was taken upon his admittance to Alcatraz Prison in 1959. He was in the middle of a five-year sentence and what happened to him in prison is incredible.

Donaldson Collection / Getty ImagesBulger claimed that he was a participant in the MK-ULTRA program while in prison, which were secret LSD experiments by the CIA. Bulger said that he was led to the program under false pretenses, and experienced sheer terror while on the drug. He was released in 1965, became a fugitive years later, and was murdered in prison at the age of 89.