It’s 2006. Paris Hilton is filming The Simple Life: season four, episode five.
She and Nicole Richie are competing to organize the best wedding for a lesbian couple and Paris wants someone to rap at the ceremony. She calls Mickey Avalon, whose self-titled debut album just came out on Interscope. Mickey shows up and performs a song about murder and suicide to the newlyweds, getting fucked on booze and god knows what else in the process.
He then steals a production van and crashes it into a wall, before fleeing the scene.
This was the height of Mickey Avalon’s fame. He had signed a lucrative album deal with a major label, his debut was a hit, largely thanks to the platinum-selling single “My Dick”, and he was rubbing shoulders with the biggest names in the music industry. Yet for every taste he had of the Y2K highlife, Mickey endured twice as many frankly astonishing events. Having made it to his 50th year, he’s overcome decades of addiction, tragic family bereavements, and a couple of half-arsed suicide attempts. He’s now found a home in a unique spot at the seedy outer edges of the music industry.
“I always said I’m gonna die by 25,” Mickey says, speaking over a video call from his home in LA. “I didn’t take good care of myself. But I don’t think I’m gonna die anytime soon. I think when you try to die and you don’t, then your curse is like, you live forever.”
He is lovely to talk to, funny, forthcoming, and open on all subjects. Our conversation lasts more than three hours.
Mickey’s story is a challenging one to tell. Two people have tried to write his biography. Both are now dead. His biggest hit lives on, but the two friends he made it with—Dirty Nasty and Andre Legacy—have had contrasting fortunes ever since. Legacy, the man whose folkloric wanger inspired the song, has faded into obscurity, while Dirty Nasty aka Simon Rex, the man who made the beat, is now a Hollywood actor, starring in Sean Baker’s 2021 comedy Red Rocket and Zoe Kravitz’s Blink Twice. Arguably the person who’s profited most from Avalon’s output is Awkwafina, whose 2012 viral hit “My Vag” was inspired by “My Dick” and helped launch the young actress’s career. But somewhere deep within Mickey’s winding 20-year story lies an intangible truth about the American Dream in the 21st century.
Somewhere.
***
Mickey was born Yeshe Pearl on December 3rd, 1975 to a Jewish family living in LA. He was the grandson of two Auschwitz survivors who fled Hungary for the States 30 years earlier. Between them, his grandfather and grandmother endured the cruel medical experiments of Josef Mengele and the attacks of Amon Goeth’s dog (the awful man played by Ralph Fiennes in Schindler’s List); they died in their nineties, living just long enough to see that their escape was worth it, leading as it did to an entry into the pantheon of great penis songs.
Where Mickey grew up, in Hollywood, the cut-off date for new starters at the nearest school was December 2nd, so his mum changed the date on his birth certificate, making him the youngest kid in his year group. He later attended Beverly Hills High School, where he started selling weed aged 14. When his mum caught him dealing in front of their house, she sat him down and set him straight. “You’re selling shit weed and smoking too much of it yourself.” She began supplying her son with better quality product and soon, Mickey was making enough money to move out.
“I always said I’m gonna die by 25”
—Mickey Avalon
Then when Mickey was about 17, his mum noticed track marks on his arm, a horrifying sight to a mother who had recently divorced her husband—Mickey’s dad—because of his heroin addiction. She fired Mickey for the same reason. “You can’t trust somebody on heroin,” she told LA Weekly in 2006. “I just saw too much of his dad in him when he was like that.”
Mickey’s dad was running with some dodgy characters, like Eddie Nash, alleged mastermind behind the Wonderland murders of 1981. Mickey’s mum later heard that one of Nash’s heavies had offered to kill her as a favor. Mickey’s dad declined the offer and, wanting to get his life back on track, started putting in time trying to get clean. He completed a year of rehab. Then one day, on his way home from an AA meeting, he was hit by a drunk driver. In hospital, when he was 19, Mickey made the decision to turn off his dad’s life support.
Both Mickey and his younger sister struggled with heroin addiction, especially after their dad’s death. A year after he died Mickey had a child with his teenage wife. They moved to Portland with their newborn, but Mickey couldn’t kick the heroin. He left his young family and checked into the St Francis Hotel, where Gus Van Sant shot Drugstore Cowboy.
One day he was arrested on an “intent to possess” charge by police posing as dealers and thrown in a cell. Among the other junkies who were locked up for the night, some rave kid told Mickey he could hook him up with drugs if he gave him a place to stay. Mickey didn’t believe him, but snuck him into his room at the St Francis on the off chance. The kid disappeared and came back 20 minutes later with the goods.
Mickey couldn’t believe it. He let the kid share his bed and asked what his secret was.
The kid showed Mickey a place called Vaseline Alley, where he would hop into the passenger seats of cars as they slowed down and their middle-aged male drivers let him in. They drove him round a corner and a short while later he was a few dollars richer. Mickey started doing the same thing, “hustling gay dudes for quaaludes,” as he described it on his subsequent album. For a long time, Mickey let people believe that his interactions with these men were sexual. These days, he says he’d pretend to offer such a service, wait until his clients’ trousers were round their ankles, then grab as much cash as he could and make a dash for it.
Eventually the rave kid caught feelings for Mickey and left. Mickey moved in with his mum, and his sister moved back shortly after. They got clean and started going to 12-Step meetings together. They both found new romantic partners.
Then, Mickey’s sister relapsed. His mum found her dead in her room while Mickey was in the shower.
Mickey soon relapsed himself, and not long afterwards made his first attempt at an overdose. He never wrote a letter, but was in a bad way. It was the night before his job interview at a bagel shop. He took all his drugs in one go and decided it would be fine if he never woke up. He came to the next day on the ground, facing his record collection. It was a disaster. Not only was he alive; he had no drugs left. Plus, he had to get to that interview. He made it and got the job. He was fired the next week and soon made another attempt at an OD, but this time he left himself a bit of product so that when he woke up the next day he could at least get high.
This was Mickey’s lowest ebb, but somehow he remained positive. “I’m not from this, like, mental health generation,” he says. “I was sad at the time, but I woke up and went on with my day. I’m pretty optimistic [about] a lot of stuff.”
Unbeknownst to Mickey, a lucky break was heading his way.
***
Simon Rex was an 18-year-old working in a potato sack factory in San Francisco when he met an aspiring model at a rave, and convinced her to move to Hollywood with her two-year-old son. They found a place to live but struggled for rent and, on his girlfriend’s suggestion, Simon filmed two self-masturbation scenes for gay porn films that were later titled Young, Hard, & Solo 2 and 3. One day, he accompanied her to an audition and got scouted by a casting director. The relationship ended, but Simon started traveling the world on modeling jobs.
Working a gig on a rooftop somewhere in downtown LA, he got talking to another model. It was Ben, a childhood friend of Mickey’s. Ben pointed at LA County Jail on the horizon and said he’d be checking in there the next day. He’d been found guilty of robbing someone with a .380 pistol Mickey had given him when they were teenagers (it was a gift to Mickey from his dad, but he’d declined it, saying: “I’m just gonna shoot my dick off or something”).
Not long after meeting Ben, Simon stumbled into a job as an MTV VJ. That led to acting work, namely in the sitcom What I Like About You and horror-comedy Scary Movie 3. In his spare time, he made hip-hop beats on a vintage drum machine. Fellow actor Adrien Brody taught him how.
After more than a year in jail, Ben emerged and reconnected with Simon. He was impressed with his beats and wanted to connect him with Mickey, who had been writing raps in his spare time along with his school friend Armen Melik. But Mickey was reluctant. He was more into painting, having recently joined the well-known LA graffiti crew CBS (Can’t Be Stopped/City Bomb Squad). Simon was even less keen on the idea.
“I was like, look man, I don’t want to meet any rappers,” he says. “I’m just doing this for fun. The last thing I need is rappers in my life.”
But Ben insisted. Eventually the connection was made and Simon, Armen, and Mickey hit it off immediately. Before long, they were calling themselves the Dyslexic Speedreaders and giving themselves rap aliases. Armen chose “Andre Legacy”, wanting to sound like America’s preeminent tennis player of the time. Simon went by “Dirt Nasty”. And Yeshe Pearl was christened “Mickey Avalon”. Andre thought it made him sound like a porn star. Completing the DS lineup was local friend and guitarist Jeramy “Beardo” Gritter.
In 2003, Simon—by now a minor celebrity—showed off his southern California pad in an episode of MTV Cribs. After twatting a punching bag with a baseball bat and pointing out a signed photo of Golden Girls’ Estelle Getty (“Simon, put it in me”), he gave his friend a short cameo, introducing Mickey Avalon to the world.
A slew of songs followed, the three of them rapping cartoonishly about crooked cops, murderous lesbians, eating disorders, and “jack-off flicks.” Unlike the chauvinist gangsta-rap braggadocio du jour, DS bragged about buying drugs and selling their bodies.
On “Waiting to Die,” the first song he ever wrote, Mickey called himself “a street walker selling cock for rock,” adding: “I used to work nights at Hot Cock Dot Com / but then I got fired when my mom logged on.” Artistic licence, he says.
One day Andre Legacy was in the shower. He looked down at his knob. Something magical happened. Ejaculate conception: instead of impregnating a woman with a child, Andre’s penis impregnated his own brain with an idea. He rushed to tell the others. They were to record a song. It would be called “My Dick”.
“Oh, I wonder what that’s about…” Simon replied. “That’s the dumbest idea.” Mickey didn’t like it either. Andre persisted. To shut him up, Simon made the most basic beat he could think of. Andre immediately started rapping: “My dick: bigger than a bridge / Your dick: look like a little kid’s.” Pretty soon Mickey joined in: “My dick: plays on the double-feature screen / Your dick: straight to DVD.” A masterpiece was born.
Simon recorded their music onto CDs and wrapped them in the dominatrix ad pages of the LA Xpress before handing them out at nightclubs around the city. He never got Mickey’s permission, but soon there were celebrities listening, including Paris Hilton and Leonardo DiCaprio, and Mickey started getting booked to play shows around LA. He usually played them with his top off—torso covered in tattoos and eyes daubed with mascara. At his first ever gig he took a Jack Daniels bottle onstage to complete the look, but filled it with apple juice because he was enrolled at a no-drinking facility at the time.
The shows became notorious. Simon thinks there were two girls for every boy at their gigs. Andre says it was more like three to one. “Like a young Mick Jagger, the singer is shirtless and skinny, ugly and pretty,” wrote John Albert in LA Weekly. Hoping to parlay momentum into a publishing deal, Simon arranged a meeting with Steve Lindsey, a music industry bigwig who’d worked with Elton John, Ray Charles, and Leonard Cohen. His next collaborator would be the “My Dick” guy. “That’s not him rapping?” Lindsey said, staring at a picture of Mickey while Simon the music. “That’s him rapping,” Simon replied. Lindsey went to the show that night and, knowing there were powerful eyes on him, Mickey dialed it up to 11. He’d moved on from apple juice and chugged a beer onstage before bringing the empty bottle crashing down on his own head. Glass everywhere. Lindsey turned to Simon and said: “I think this guy’s a star.” He sang Mickey’s praises to LA Weekly, comparing his androgynous style to David Bowie.
“At his first ever gig he took a Jack Daniels bottle onstage to complete the look, but filled it with apple juice because he was enrolled at a no-drinking facility at the time”
Interscope released Mickey’s first single “Jane Fonda”. It reached number 36 on the Billboard Modern Rock chart, and his self-titled debut album was a success. Meanwhile, Simon’s acting career was taking off. Scary Movie 3 was a hit and he also made an appearance in the UPN sitcom Cuts, alongside Meghan Markle. Years later British tabloids would offer him $70,000 to say that he’d slept with Meghan at the time. He refused.
His Blackberry was buzzing, his agents calling to talk about auditions. “Where are you?” they asked. “Oh, I’m in Poland,” Simon told them. “I’m opening for the Red Hot Chilli Peppers.” They didn’t know what he was talking about. “What do you mean? You do music?” they asked. “Well,” Simon replied. “I guess so.” Eventually the Blackberry stopped ringing. But he didn’t care. He was having the time of his life.
In 2009, Mickey was invited on Snoop Dogg’s Blazed and Confused tour. After his set at the Santa Barbara Bowl, Mickey’s girlfriend lit a cigarette in the dressing room. “You can’t smoke here,” said a stocky security guard with glasses. The girlfriend put out the cig, but he still wasn’t happy. “Chill out bro,” Mickey told him. He wouldn’t. Mickey snatched the glasses off the man’s face. The guard disappeared and returned with a burly colleague, sparking a scuffle. Mickey slammed a fist into his cheek. The photograph that ran in the newspaper the next day also provided the original cover of Mickey’s 2009 single “I Get Even”.
A reputation for chaos started following Mickey around. “I wouldn’t say he has a screw loose…” says Simon. “But he’s a crazy motherfucker.” All the while, Mickey never stopped taking drugs. He smoked heroin. He injected it. He injected cocaine. He tried GHB before a show, but took twice the usual dose and once he got onstage, struggled to operate his mouth.
Desperate to put on some kind of show, he attempted a stage dive. He landed on a girl who he says must have weighed no more than 80 pounds. The wheels were starting to spin.
Needing a second album, Interscope boss Jimmy Iovine put Mickey in a studio with Dr Luke, songwriting partner to Kesha, Taylor Swift, Avril Lavigne, Kelly Clarkson, and Pink. Luke was so big he had a team of minions making Mickey’s beats, including one Benjamin Levin, who later changed his name to Benny Blanco. Luke suggested Mickey make a song with another prodigy, “the girl who did that song ‘I Kissed A Girl’,” as Mickey told BVTV. They recorded a track, but the ascendant singer’s people weren’t keen on it ever seeing the light of day. They told Mickey he could credit his collaborator only as Kitty Purry.
The Dr Luke sessions were unsuccessful. “I’m the only project he’s ever worked on that didn’t go far,” Mickey told RapReviews. His relationship with Interscope soured. He heard that his manager turned down an approach from Dr Dre, who wanted to remix “My Dick”; the manager insisted the song was perfect as it was. Eventually the Interscope contract was terminated.
Then, Mickey fell out with his closest friend.
“After years of touring all over the world, like every rock band story you hear, we were ready to kill each other,” Simon says. He and Mickey got into a disagreement somewhere in Australia. Something to do with money. They didn’t speak for years.
The Dyslexic Speedreaders went their separate ways. Mickey’s second album Loaded finally arrived in 2012, on the indie label Suburban Noize. Simon went on tour with Charlie Sheen, flying between shows on private jets and performing Dirt Nasty solo material until the crowd chanted for a refund. He teamed up with Riff Raff and comedian Andy Milonakis to form Three Loco, another boisterous rap group signed to Diplo’s label Mad Decent, which provided Simon with another dose of the hedonistic touring life.
Andre released some solo music too, but during the 2010s they largely faded into obscurity.
After years of silent beef, Mickey and Simon arranged a time and a place to square their differences with a fistfight.
When they both arrived, Simon suggested they sack it off and get high together instead, which they did.
Over the next few years, they began cleaning themselves up. Director Sean Baker offered Simon the lead role in Red Rocket, a film about a washed-up but lovable ex-pornstar. It earned a standing ovation at Cannes and Simon was crowned a born-again star. Mickey stopped taking drugs. Andre didn’t. In contrasting ways, middle age arrived for all three.
***
Many people who move to Hollywood in search of stardom encounter a nightmare—a shady world of darkness and deception—and leave, or worse: resort to drugs, sex work, or suicide. The lucky few become stars by adapting to the darkness, but Mickey was born in it. He became a star almost against his will, having already experienced the drugs, the sex work, and the suicide attempts. While rappers of his day bragged about selling drugs, Mickey bragged about taking them. And on his biggest hit of all, he sold his own manhood to the music industry.
It’s hard to imagine someone like Mickey landing a major-label record deal in 2025. “My Dick” was released into a world where celebrity sex tapes permeated the internet and unflattering photos of Britney Spears sold magazines. Mickey’s biggest hit spoke to a generation of frat boys who had grown up idolizing Hank Moody and Vincent Chase. Yet the rest of his catalog offers a decidedly more complex image of masculinity, of a man who once bragged about dishing out hand jobs while wearing eyeliner. Maybe the real triumph of his story is simply that someone who seemed to have lost everything made it big because they made good music and their friend handed some CDs out at local clubs.
Maybe the real triumph of his story is that he’s still alive to tell it.
“The lucky few become stars by adapting to the darkness, but Mickey was born in it”
“In a weird way, I feel like everything happened the way it was supposed to,” Simon says. “If [Mickey] had gotten completely sober when he began his career, and wasn’t punching security guards, maybe things would be different. But then if he did blow up and make it really huge, he might be dead now.”
Today, Mickey lives with his fiancée and manager, who goes by Minnie Avalon, somewhere in LA. He still plays shows around the U.S. on a regular basis, and limits his indulgences to a bottle of wine a day. “It sounds like more than it is,” he says. “It’s really just four cups.”
He has a few regrets, things he would have done differently, but ultimately credits his success to his friends for putting him in front of the right people.
“I tried as hard as I could to fuck it up. And I didn’t,” he reflects. “Still trying, though.”
If you’re struggling with addiction, you can visit the official website of SAMHSA’s National Helpline for treatment information.
If you or someone you know is considering suicide, help is available. Call 1-800-273-8255 to speak with someone now or text START to 741741 to message with the Crisis Text Line.
Follow Sam Davies on X @samdavies313
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