Sean Penn should have it made - so why doesn't he? Photo / Getty Images
Sean Penn should have it made - so why doesn't he? Photo / Getty Images
Sean Penn really should have it made.
The critically acclaimed actor has won numerous accolades, including two Academy Awards for Best Actor for his roles in Mystic River and Milk as well as five additional nominations.
But the actor is famously outspoken and deeply politically motivated.
He's cultivated friendships with dictatorial leaders and drug king pins, he's publicly attacked the creators of South Park, he's made unusual statements about the #MeToo movement multiple times and early in his career allegedly had SWAT teams called to his home.
Penn and Madonna were married from 1985 to 1989, during which time he allegedly was involved in a physical altercation with his wife. No charges were ever laid.
According to reports, Penn was already in trouble with the law at the time for violently attacking an extra on set. He was sentenced to 60 days for this assault, as well as the judge ordering he undergo six months of psychotherapy. Penn ended up serving 33 days of his sentence in the Los Angeles County jail.
After he was released from prison, he returned to his wife Madonna but they started fighting again. The couple separated for some time in 1989, but it wasn't the end for Madonna.
According various reports from the period, on December 28, 1989 — while the couple were separated — Penn scaled the wall of their Malibu home and found Madonna, who was alone.
She was able to escape and made her way to a police station.
"I hardly recognised her as Madonna. She was weeping, her lip was bleeding," Lieutenant Bill McSweeny said.
Madonna filed for divorce the following week.
The Holiday singer has since flatly denied the allegation that Penn had attacked her, in any way.
Madonna filed a sworn affidavit that said, "Sean has never struck me, 'tied me up', or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless, and false."
Madonna and Sean Penn pictured in 1986. Photo / Getty Images
Addressing the media coverage of the events numerous times over the years, she has claimed that they are a complete fabrication and that none of the events ever occurred.
However, a New Yorker piece concluded that from their investigations, tabloid reports that Penn had been arrested were incorrect but confirmed Madonna did indeed summon the SWAT teams to the couple's home.
And contrary to Madonna's flat refusal of any of the events taking place, Penn did partly acknowledge the marital scuffle in a Playboy interview. He said a "SWAT team surrounded my house and came in every door," on the day they split up.
Penn explained that "they were coming up there ostensibly to keep her from getting a haircut and to let her gather some personal effects," explaining his wife had been alarmed by his collection of guns. He said no charges were filed.
PENN GETS INTERVIEW SUBJECT ARRESTED
Penn loves to be political and engage in transgressive work, and has taken a recent foray into serious journalism. And in 2016 he interviewed drug lord Joaquín "El Chapo" Guzmán for Rolling Stone in the interest of sparking debate about the war on drugs.
He described the brutal kingpin's methods of execution-style head shots as "pragmatic" and his tunnelling systems for transporting large volumes of illicit drugs from Tijuana to San Diego as "accomplished" feats of engineering. In the interest of context, the death of thousands of individuals have been personally attributed to El Chapo.
Penn referred to El Chapo as a "president of Mexico" and a figure of Mexican folklore.
Explaining the situation of brokering the interview to the readers, Penn described himself in a situation that he said was "compartmentalised".
"The trust that El Chapo had extended to us was not to be f***ed with," he wrote.
Penn organised a deal with the drug lord that he would give him final edit and control of how he was portrayed in the piece.
On the same day the interview was published, El Chapo was arrested by Mexican authorities. They attributed Penn's article to leading them to the arrest.
"Let me be clear. My article has failed," Penn said in 2016.
Sean Penn with Charlie Rose. Photo / Getty Images
"I have a terrible regret," Penn told CBS journalist Charlie Rose. "I have a regret that the entire discussion about this article ignores its purpose, which was to contribute to this conversation on the war on drugs."
And while Penn has tried to put the incident behind him, in April this year the US Attorney's Office filed a motion requesting portions of Penn's audio recordings with El Chapo to assist with their prosecution of the drug lord. The recordings could make up the key to building their case against him.
SEAN PENN WROTE AN EXTREMELY STRANGE BOOK
In March of this year, Penn published his first novel, Bob Honey Who Just Do Stuff. This book was originally to be published under the very clever pseudonym Pappy Pariah, and Penn was clever enough to even invent a backstory for Pariah, saying he met the author in 1979 at a bar in Florida.
The book, now attributed to Penn, is described as a "darkly funny novel" about a man who is tired of stuff. He's tired of "being marketed to every moment," and he's tired of "the media" and "nosy journalists" and "a world where even an orgasm isn't real until it is turned into a tweet".
The book was not received well by critics, who described it as a thinly veiled cipher for Penn's personal rage about, well, everything, from US politics (both on the left and right) to the #MeToo movement, advertising, Hollywood and gun ownership. Huffpost called it a "160-page self-own." It is full of big words and unusual sexual imaginings, including dream sequences where Penn's protagonist has a sexual relationship with a hairless woman.
The novel contains numerous scenes of violence, including the protagonist murdering pensioners with a mallet in the service of reducing their carbon footprint. He also lights a dildo on fire and ends his novel with a hyperviolent killing spree.
SEAN PENN CALLS #METOO A 'RECEPTACLE OF THE SALACIOUS'
Sean Penn has been outspoken about his controversial views. Photo / Getty Images
Penn was interviewed by The Today Show in the US for his TV show The First, where the interviewer asked him about his co-star Natascha McElhone's female character. Characterised as a "strong woman" the host asked if her leading role was at all informed by the #MeToo movement.
Penn took the opportunity to give rambling and mostly inscrutable review of the Hollywood movement, which has been informed by many high profile women coming forward with stories of sexual assault.
"I'd like to think that none of (the show's plot) was influenced by what they call the movement of #MeToo. I think it's influenced by the things that are developing in terms of the empowerment of women who've been acknowledging each other and being acknowledged by men," Penn said.
"This is a movement that was largely shouldered by a kind of receptacle of the salacious."
When the interviewer asked Penn to clarify, he kept digging.
"The spirit of what has been the #MeToo movement has been to divide men and women.
"The women that I talk to, in real life, not in front of a camera, that I listen to, of all walks of life, there's a common sense that is not represented at all in the media discussion of it. Where if Sean Penn says this, so and so is going to attack him."
During the largely inscrutable rant, McElhone looked deeply bored and vaguely disturbed while Penn got more and more red in the face. She said they had discussed the #MeToo movement at length on set and explained Penn had issues with actors who had "got a lot of attention" for airing their stories of assault.
PENN ATTACKED SOUTH PARK CREATORS
Penn is no stranger to a lengthy and pointed rant. In 2004 he wrote an open letter to the creators of South Park, Trey Parker and Matt Stone.
Stone had made comments in Rolling Stone that people who felt uninformed about politics shouldn't feel pressured to vote.
"If you don't know what you're talking about, there's no shame in not voting," Stone said.
In an open letter, Penn begins by accusing Stone and Parker of "(trading) on my name."
"When anybody who doesn't have a child, doesn't have a child at war, … or won't be in harm's way themselves, is encouraging that there's 'no shame in not voting'.
"No one's ignorance, including a couple of hip cross-dressers, is an excuse.
"All best, and a sincere f**k you," he concluded.
"I was so surprised." Stone said of receiving the open letter. "Basically, it's some sort of alien logic."
AFTER SPLITTING WITH CHARLIZE, PENN ADOPTS YOUNG LOVER
Penn and Charlize Theron got together in December of 2013 and became engaged in 2014. but called of the relationship in 2015.
In 2016, Theron gave a clipped response when asked about the relationship breakdown.
"It's just its own beast. We were in a relationship and then it didn't work anymore," she said. "And we both decided to separate. That's it."
Penn, 58, has been dating 26 year old actor Leila George for the last two years. Penn and her father are the same age, while her mother is one year his junior.
