Musicians are just as corruptible as the rest of us. It is commonplace now to see your favorite musicians in trouble with authorities for drug charges or drunken stupors. Drug- and alcohol-related arrests have become something of a staple of the music industry.

However, in rare circumstances, musicians get into trouble for the unlikeliest of transgressions. These strange criminal blunders are undoubtedly rare among musicians, but they are so puzzling and hilarious that they deserve a light shining on them.

10 Paul McCartney

In 1960, former Beatle Paul McCartney was arrested in Hamburg, Germany, for attempted arson. McCartney and then–Beatles’ drummer Pete Best pinned a condom to the wall of the Bambi Kino, their accommodations while playing in Hamburg, and set the condom on fire.

After living in filthy conditions during the early string of shows, Paul’s arson was a boyish act of protest against the Bambi Kino owner Bruno Koschmider. Renowned for beating customers with a chair leg, Koschmider had put up the Beatles in the back of his porno cinema while they tirelessly played for him in his run-down strip club known as the Indra.

As George Harrison, then 17, was already being deported from Germany for flouting Hamburg’s curfew laws for minors, the Beatles were ready to go home—but not before McCartney and Best set the condom alight.

Koschmider subsequently rang the police, who arrested and detained Best and McCartney before deporting them.^[1]

9 Barry White

Before he had a music career and was nicknamed the “Walrus of Love,” Barry White was something of a criminal in his teens (by his own admission). However, White was hardly a master criminal as evinced by his arrest in 1960 for the theft of car tires which led to subsequent jail time.

As a teenager, White often got into trouble with his brother, Darryl. Barry stated that they were a “two-man gang, respected and feared [who] ran and ruled the streets of our neighborhood.” However, the theft of $30,000 worth of Cadillac tires landed him in prison.

Barry White served four months in prison in 1960. While he was incarcerated, the seeds of the Walrus of Love were sown because White vowed to do away with his minor criminal past and focus on music.^[2]

8 D’arcy Wretzky

D’arcy Wretzky, former bassist for the Smashing Pumpkins, was arrested and eventually imprisoned in 2011 due to her horses escaping her home. Wretzky’s neighbors contacted the police after her horses were left to wander from her farm onto their land. Although she was notified of the offense in 2009, it took until 2011 before her antics led to prison time.

Michigan has an “animals running at large” law that Wretzky breached. However, the law is only a minor offense. It was Wretzky’s repeated absence from four consecutive court dates related to the incident that eventually landed her in jail.

Otherwise, Wretzky would have only had to pay a fine. Nevertheless, she was sentenced to six days imprisonment.^[3]

7 Gary Numan

New wave singer and songwriter Gary Numan found himself on the wrong side of Indian police in 1981 when he was arrested on suspicion of smuggling and spying. As an air display pilot as well as a musician, Numan was flying with a friend over India. After the plane’s engine gave out, they were forced to land.

The pair sought help in a local Indian village but instead were arrested on suspicion of smuggling and spying. As the two men were wearing two watches each, the police thought they were smuggling. Worse still, the pair had cameras on them which gave the police grounds to believe that they were spying.

Little did Numan know, there was actually a Russian submarine base 32 kilometers (20 mi) from where they had landed. Therefore, the Indian police thought that they were taking photographs of that base.

Both Numan and his friend were arrested and detained for four days. Eventually, the pair contacted the Home Office, and they were duly released.^[4]

6 Vanilla Ice

Rapper (sort of) Vanilla Ice got in trouble with authorities in 2004, albeit for something far less sinister than his arrest for burglary in 2015. In fact, it was animal control officials that landed Vanilla Ice in difficulty.

Vanilla Ice’s pet wallaroo, Bucky Buckaroo, and his pet goat, Pancho, decided one day to escape Vanilla Ice’s domicile in Florida. Pancho managed to headbutt open the latch of the gate of their enclosure, and the two went for a ramble in Florida.

The rebellious animals actually scratched one woman and kicked her car after she tried to feed them. Animal control officials eventually captured the two, and their days on the lam were cut short.

Animal control officials caught Vanilla Ice with an expired permit and duly fined him $220. Pancho and Bucky were eventually reunited with their owner.^[5]

5 Peter Buck

REM’s guitarist Peter Buck was arrested for an air rage incident in 2001, but the story was far sillier than it sounds. After allegedly making the mistake of mixing a sleeping pill with alcohol, Buck went on a drunken rampage, much to the chagrin of his fellow passengers.

After being refused any more alcohol, Buck in his already-drunk, loutish state overturned a flight attendant’s trolley and demanded to leave the airplane mid-flight. He had to be pulled away from an exit door. As a pilot attempted to calm the situation, Buck responded that “he was just a f—king pilot and [Buck] was REM.” Even stranger, Buck sprayed flight attendants with yogurt and tried to steal cutlery from the plane.

The guitarist was later cleared of all charges, and he did help to clean up the yogurt mess while on the plane.^[6]

4 Bob Dylan

New Jersey police detained poor old Bob Dylan in 2009 over a simple case of mistaken identity. The icon of folk music was set to headline a concert alongside Willie Nelson and John Mellencamp. But it nearly didn’t happen thanks to New Jersey police officer Kristie Buble, who believed that Dylan was a mad pensioner who had escaped from a hospital.

Dylan went for a stroll around the Long Branch area on his own in the pouring rain when a concerned citizen rang the police about the suspicious-looking character. When Buble arrived to determine what was going on, Dylan told her that he was indeed Bob Dylan. But for the police officer, that just confirmed her suspicions of a madman on the loose.

Apparently forgetting that people age, Buble expected Dylan to look like her memories of him from his younger years. As a result, Buble believed that the man in front of her was a rambling lunatic and not Bob Dylan.^[7]

Detained by the police, the musician was taken to his nearby tour bus to confirm his identity. When they reached Dylan’s manager, he showed Dylan’s identification to the now-embarrassed police officer. In her defense, it was a little strange that Dylan was wandering around in the rain, but he’s never been one for conventional behavior.

3 Mick Jagger, Bill Wyman, And Brian Jones
The Rolling Stones

Although two of the Rolling Stones, Mick Jagger and Keith Richards, were infamously arrested and charged with drug offenses in 1967, it was public urination that saw three of the Rolling Stones—Bill Wyman, Mick Jagger, and Brian Jones—arrested in 1965.

After being refused access to a petrol station lavatory in London, three of the Rolling Stones took it upon themselves to relieve their full bladders by urinating on the petrol station itself. The unsympathetic station owner had denied Bill Wyman the key initially. However, Jagger and Jones also took offense at this.

All three began chanting “we’ll p—s anywhere, man” to the station owner and a nearby mechanic who had witnessed the scene and was merely attempting to move them on. When the owner wouldn’t concede, Jagger, Wyman, and Jones urinated on the wall of the petrol station while still chanting.

After the trio was arrested, they were charged with public indecency and subsequently fined £5 each.^[8]

2 Frank Zappa

In the early years of Frank Zappa’s career, he was not too discerning about where his much-needed money came from. This became painfully apparent in 1962 when Zappa was duped into making porn for an undercover San Bernardino police detective in California.

After creating several scores for low-budget films, Zappa was offered work by a supposed used car salesman to produce a porn film. As the “used car salesman” knew of Zappa’s amateur film credentials, he turned to Zappa for help.

Though Zappa refused to outright make a porn film for the man, Zappa did offer to record audio-only porn with his friend Lorraine Belcher in a studio owned by Zappa. The recording was essentially a mock-up of a couple having sex.

After Zappa made the recording, the “salesman” refused to pay him. Instead, the police raided the studio and seized the tapes. Of course, the “used car salesman” was simply an undercover detective hoping to entrap an unwitting “criminal.”

Zappa was charged with conspiracy to make pornography and given a 10-day prison sentence. This made Zappa a lifelong cynic toward authority.^[9]

1 Ozzy Osbourne

Yet more public urination from a beloved rock star. Throughout his lengthy career, Ozzy Osbourne has been a staple of the typical rock and roll antics that define the genre’s more reckless practitioners.

Ozzy is the epitome of the drunken, drug-induced wild behavior of rock stars. Some of his most outrageous behavior included biting the head off a bat and snorting a line of ants. But in 1982, a drunken Ozzy was arrested for urinating on a historic landmark.

In a drunken stupor, Ozzy stumbled around San Antonio, Texas, looking for a place to relieve himself. Unfortunately, he chose the city’s Cenotaph dedicated to the fallen soldiers in the Battle of the Alamo.

To make this story even stranger, Ozzy was wearing the clothes of his wife, Sharon, the whole time because she had denied him access to his own so that he could not go out and drink. Obviously, it didn’t work. The police arrested Ozzy for public intoxication. He was freed on $40 bond the same day.^[10]

Edward is a writer and musician.

That cute emoji could get you in trouble. In the past few years, there has been an increase in emoji-related convictions. This happens because emojis can be used in place of real-life objects. For instance, sending a gun emoji to a person could be considered a death threat.

Others involved in noncriminal issues have received hefty fines or experienced avoidable inconveniences for using supposedly innocuous emojis to convey their emotions and reactions.

10 An Israeli Couple Was Fined After They Unwittingly Sealed A Deal With Several Emojis

In 2017, an Israeli couple discovered that emojis are not playthings after they received a $2,200 fine for using these types of images during a deal. Trouble began for Rosen and Nir Haim Saharoff when they started negotiations with Yaniv Dahan over an apartment he had for rent.

Dahan and the couple exchanged several text messages about the apartment. The couple used several friendly emojis during the conversation, causing Dahan to think they were going to take the apartment. In fact, he deleted the online listing for the apartment.^[1]

However, the couple suddenly stopped replying to his messages. Dahan took them to court and successfully argued that the series of emojis the couple used during their conversations made him believe that they were interested in the property.

The couple used the emoji of a dancing lady, two people dancing, a chipmunk, a peace sign, a smiley face, and a champagne bottle. The Saharoffs claimed that they backed out of the deal because they did not like the apartment. That did not fly with the judge. He said that the use of emojis created “a great sense of optimism.” He ordered them to pay $2,200 to Dahan.

9 Teen Arrested For Pointing A Gun Emoji At A Police Emoji

In 2015, a teenager was arrested for pointing three guns at a police officer. Besides the obvious question of how the teen managed to aim three guns with only two hands, the arrest wouldn’t have raised an eyebrow if the guns and police officer had not been emojis.

The emoji was part of several pictures and captions that 17-year-old Osiris Aristy had posted on his Facebook wall. He wrote, “N—a run up on me, he gunna get blown down.” Then he added the emoji of a police officer and three guns. In another post, Aristy wrote, “Feel like katxhin a body right now.”

The teen added several other pictures where he posed with guns and drugs and made gang signs. The NYPD arrested him after they were tipped off about his threatening posts. Aristy was charged with illegal possession of weapons, drugs, and “making terrorist threats.”^[2]

Police said that this was not Aristy’s first run-in with the law. In fact, he had been arrested 12 times for alleged crimes such as illegal possession of a weapon and drugs as well as an assault. He often posted about owning a gun and was under surveillance at the time he made the emoji posts.

8 Man Receives Jail Term For Sending Gun Emoji To Ex

In 2016, 22-year-old Bilal Azougagh was sentenced to six months imprisonment for sending a gun emoji to his ex. The emoji was part of a series of distasteful messages he sent to the unnamed woman after they broke up.

The ex pressed charges after receiving the emoji, which she considered a death threat. Her counsel argued that the messages and emoji made her afraid and caused her nightmares. Azougagh’s counsel disagreed, saying the emoji had no serious undertone.

The court sided with the woman and determined that the emoji was a death threat. Azougagh received a six-month sentence and was ordered to pay €1,000 in damages. He was lucky, though. Under French laws, a death threat could lead to three years in prison and a €45,000 fine.^[3]

7 Man Arrested For Sending X-Rated Emojis To Teen

Emojis sometimes have sexual undertones. This could quickly lead to problems when they are sent to minors. Ask the unidentified 53-year-old Australian man who was arrested for sending inappropriate emojis to a minor.

The unnamed man had earlier been arrested for trying to groom minors. He was released on bail. Weeks later, he returned to what he knew best and attempted to groom another 12-year-old via social media and text messaging. Instead of using regular words, he used emojis.

Police did not reveal the emojis used by the man. However, they said that he was charged with “sexual assault, indecent treatment of children under 16, and indecent treatment of children under 12.”^[4]

6 Two Men Arrested For Sending Threatening Emoji To Another Man

Threatening emojis do not always have to be about guns. Fist emojis can also be threatening.

In 2015, police in South Carolina arrested two 29-years-olds, David Fuentes and Matthew Cowan, for sending the emojis of a fist, a hand that looked like a gun, and a white ambulance to an unnamed man.

Interestingly, unlike the other emojis that got people into trouble, the men involved did not add any text to the messages. It was just the emojis. Police said the images meant the duo intended to beat up the unnamed victim so badly that he would need to be transported to a hospital in an ambulance.

Previously, Fuentes and Cowan had gone to the unnamed man’s house where they attempted to beat him up. Although the police did not arrest them for the attempted assault, officers stepped in after the men sent the emojis. Fuentes and Cowan were charged with stalking.^[5]

5 Australian Man In Trouble For Sending Gun Emoji To His Ex

Thirty-nine-year-old Jayde Booth from Barrack Heights, New South Wales, Australia, was arrested for sending an emoji of a head and a gun to his ex. Booth remained in contact with the unnamed woman after their breakup and often sent her harassing messages.

The unnamed ex had a restraining order against Booth. However, he disobeyed the order and continued to harass her. He sent her a series of messages, including one that contained the emoji of a head with a gun pointed at it.^[6]

Booth also left trash in front of her home. The woman became so scared over the frequent harassment that she fled her home. The proverbial last straw came when Booth called her six times from a private number. She contacted police after she discovered Booth was the caller.

4 Man Gets Jail Term For Sending Airplane Emoji To Ex

Even seemingly nonthreatening emojis—like that of an innocuous airplane—can get people in trouble. In 2017, 26-year-old Sloane Cruise Coake was arrested for sending the emoji of an airplane to his ex.

The couple had lived in Porirua, New Zealand, before they broke up. The unnamed woman later left for Dunedin. Coake remained in contact with her and often sent her harassing messages on social media. The ex got fed up and had a restraining order issued against Coake.

The undaunted Coake remained in contact with her anyway. He even booked a flight to Dunedin and sent her a message, “You’re going to f—ing get it.” He ended the message with the emoji of an airplane.

Judge Kevin Phillips was not familiar with emojis. He even had to ask Coake’s counsel, Sarah Saunderson-Warner, what an emoji was. Saunderson-Warner replied, “It’s one of the little characters sent after a text.” He asked if she used them, and she said yes.

Then Phillips asked if the emoji in question had been “a smiling one.” Saunderson-Warner answered that it was an airplane. Phillips promptly concluded that Coake was planning to travel to meet his ex. The judge sentenced Coake to eight months in prison.^[7]

3 Woman Unable To Use Bank App Because Of Emoji

This incident doesn’t involve an arrest. In 2016, Laurie Stark was unable to access the banking app on her phone because she had used an emoji as the nickname of her account.

Trouble began when Stark changed her nickname over fears that she could be hacked. Instead of using a name, she opted for the nail polish emoji. She did not realize what had happened until she attempted to deposit a check with her banking app.^[8]

After series of failed attempts, she contacted support. They told her to remove the emoji from her nickname and that it had even broken their system. Stark was finally able to use the app after changing her nickname to letters.

2 Teen Arrested For Adding Gun, Bomb, And Knife Emoji To Instagram Post

In 2015, an unnamed female 12-year-old student at Sidney Lanier Middle School in Fairfax, Virginia, found herself in trouble after issuing threats against her school. The girl made the threats on Instagram using the account of another student. In one post, she wrote “Killing” and added a gun emoji. Another read “meet me in the library Tuesday.”

The most controversial message included the words, “Watch out, I’m coming.” It was followed by the emojis of a gun, knife, and bomb. The unnamed girl also uploaded a list of students whom she hated and threatened to attack the school on December 15.

The school resource officer traced the posts to the unnamed student, who was promptly arrested and charged with a felony. Her mother said that the girl never planned to attack anybody and was only fed up with being bullied in school. Police later released the girl after investigations revealed that she did not intend to execute the threat.^[9]

1 Teacher Fired For Sending Eggplant Emoji To Student

Armando Alejo was a teacher in South Miami, Florida, until he was fired and banned from teaching for 10 years over a series of sexual messages he sent to a student. The messages included the emojis of a peach and an eggplant, which are used to represent the buttocks and penis.

The saga began when Alejo informed the unnamed 17-year-old student that he had barely passed his test with just under 54 percent. The student asked if there was any way that he could earn extra credit. Alejo started sending him inappropriate messages.

In one message, he wrote, “Convince me [winking emoji]. I’ll give you the B if you give me the D.” In another message, he told the student to “f—k that booty.” The student stopped replying and said he would just go with his average score.^[10]