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He's done both selfless acts and controversial things.
By Nia Tipton — Written on Feb 28, 2022
While many regard Sean Penn as a renowned actor, director, and producer, who has won two Academy Awards during his career, he is also a rather hands-on activist who often donates heaps of money to organizations and causes that he is passionate about.
Throughout his career, Penn has either garnered hoards of support from his fans over selfless acts or has been the recipient of major backlash over a controversial incident that graced headlines.
Maybe that's what makes Sean Penn so interesting — the fact that despite being an extremely polarizing figure in Hollywood, he can somehow create conversations around important topics.
Here are 6 things Sean Penn did that made people love him or hate him for it:
1. Sean Penn is on the ground in Ukraine working on a documentary about the Russian invasion.
Photo: Instagram Story | zelenskiy_official
According to Variety, Penn recently flew to Ukraine to complete a documentary on the Russian invasion with Vice Studios. Penn also appeared at a press briefing in the Ukraine capital of Kyiv listening to government officials speak about the crisis.
This isn't the first time Penn has visited the country, with his last visit being in November 2021, where he first started preparing for his documentary by visiting with the country’s military.
The 61-year-old actor is being praised by many, including the President of Ukraine. The Office of the President issued a statement through the Ukrainian embassy praising Penn for his efforts and diligence, according to Newsweek.
"Sean Penn is demonstrating bravery that many others have been lacking, in particular some Western politicians. The more people like that — true friends of Ukraine, who support the fight for freedom — the quicker we can stop this heinous invasion by Russia.”
2. Sean Penn interviewed El Chapo while he was still a wanted fugitive.
In January 2016, Sean Penn published an article with the Rolling Stone of his meeting and interview with drug lord Joaquín “El Chapo” Guzmán. However, instead of receiving praise, Penn was met with hoards of backlash over the interview.
The interview had been published one day after Guzmán's recapture by authorities, but according to Penn, he had initially done the interview during a time when the drug lord had been a fugitive after his escape from federal prison.
While there had been some readers who were taken by the sheer oddness of the interview, there were some who had an issue with the tone of the piece, feeling as if Penn had glossed over Guzmán's history as a violent drug trafficker, according to Fortune.
However, it seemed the interview eventually helped Mexican authorities to locate Guzmán and arrest him.
Even though Mexican government sources told ABC News that Penn had been under investigation for the interview, authorities also told the Associated Press, according to Fortune, that it was his meeting with Guzmán that allowed them to first locate the drug lord, in an ultimately aborted raid.
However, Penn later expressed regret over the failed interview, claiming he had "failed," according to The Guardian.
“Let me be clear. My article has failed,” Penn said. “I have a terrible regret," adding, “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.”
3. Sean Penn's alleged abuse against Madonna.
Since Madonna's marriage to Sean Penn during the 1980s, varying degrees of rumors and allegations have arisen, alleging that Penn is guilty of assaulting Madonna during their relationship.
Many of the questions surrounding the allegations, which all center around an infamous and mysterious altercation that Penn and Madonna had in their Malibu home in 1988, were all brought back to light after Penn filed a $10 million defamation lawsuit against filmmaker Lee Daniels, according to The Hollywood Reporter.
In 2015, Penn filed a suit against Daniels, claiming that the director "falsely asserted and/or implied that Penn is guilty of ongoing, continuous violence against women.” According to the lawsuit, Penn's lawyers also revealed that the actor “has never been arrested, much less convicted, for domestic violence.”
However, according to the Washington Post, Madonna was once hospitalized after Penn struck her with a baseball bat. The actor was later charged with domestic assault in 1988 and pleaded guilty to a misdemeanor.
Madonna has since denied that she was abused by Penn during the course of their marriage, even offering evidence for Penn's lawsuit against Daniels, according to The Guardian.
She even called her ex-husband “caring and compassionate," in a statement included in the lawsuit.
“I am aware of the allegations that have surfaced over the years accusing Sean of incidents of physical assault and abuse against me,” she wrote. “Specifically, I am aware of the allegations concerning an alleged incident that occurred in June 1987, whereby (according to tabloid reports) Sean allegedly struck me with ‘a baseball bat’. I know the allegations in those and other reports to be completely outrageous, malicious, and false."
While many people believe that Penn did not abuse Madonna, there are some who can't be convinced otherwise.
"I haven't forgotten how Sean Penn beat the sh-t out of Madonna," wrote on Twitter user.
There were also some who brought up his documentary in Ukraine as an opportunity for him to paint himself in a better light following the allegations of abuse.
4. Sean Penn filmed a documentary after the earthquake in Haiti.
After the 7.0 earthquake that left the country of Haiti in devastation in 2010, Sean Penn traveled to the island, documenting the aftermath, according to Entertainment Weekly.
The Discovery+ documentary, titled 'Citizen Penn,' follows Penn over the course of 10 years as he and a team of volunteers set up a long base to bring aid to Haitians, including through his non-profit organization called CORE.
"From climate to conflict resolution, to poverty and COVID-19, citizenship increasingly requires service. Service itself can be a bumpy road, but one we all have to travel," Penn said in a statement to EW.
During the tragic earthquake in Haiti, an estimated 300,000 people lost their lives, while hundreds of thousands of Haitians were injured, and 1.5 million were left with homes, according to USA Today. The country has still not been able to recover.
“I saw him hurriedly set up some way for a plane to get into Haiti with supplies, watched it right in front of me,” The director of 'Citizen Penn,' Don Hardy, told The Guardian. “He was on the first plane he could get."
"I reached out to his assistant to ask if Sean needed someone there on-site to film what was going on, and she said yes," Hardy continued, seemingly praising the actor. "A couple of weeks later, myself and a few friends were there on the ground shooting footage that could go out to news organizations and show what was going on.”
5. Sean Penn once got into an altercation with an extra on the set of his movie.
Photo: Jaguar PS | Shutterstock
During the filming for his 1988 movie, 'Colors,' Penn reportedly got into an altercation with movie extra Jeffrey Klein, according to the LA Times.
According to a spokesman for the city attorney’s office, Penn objected to Klein’s photographing him and fellow actor Robert Duvall, proceeding to swear and spit at him.
When Klein had spit back, Penn punched him in the face several times with a closed fist and had to be pulled off him and restrained by members of the crew and cast. Klein was treated for cuts and bruises at an emergency medical care center.
That wasn't the only incident Penn found himself in during that time, having to spend 60 days in County jail for reckless driving. Los Angeles police stopped the actor on suspicion of drunk driving after he sped through a red light. Penn failed field sobriety and breath analysis tests but the charge was reduced to reckless driving in a plea bargain with the city attorney’s office.
6. Sean Penn helped ramp up COVID-19 testing in Los Angeles.
According to The Hollywood Reporter, during the summer of 2020, Penn and his Community Organized Relief Effort nonprofit, also called CORE, helped Los Angeles to reach maximum testing capabilities.
In late May 2020, Los Angeles Mayor Eric Garcetti announced the opening of a new COVID-19 testing site at Dodger Stadium in partnership with CORE. Operated by CORE and LAFD, this site had the capacity to test 6,000 residents a day free of charge, which made it three times the size of any other location in L.A. County and said to be the largest testing site in the U.S.
It came after CORE started operating free COVID-19 testing sites across the country, focusing on making sure people in underserved communities, communities of color, first responders, and essential workers, were able to get tested.
Penn has also been a strong advocate for vaccination against the virus, even refusing to continue his work on the show 'Gaslit,' until every member of the show's cast and crew has been vaccinated, according to Deadline.
Through his organization, Penn reportedly offered to facilitate the vaccination effort, making it free of charge. "I think it should be as mandatory as turning on your headlights on a car at night," Penn told USA Today. "I will go back to work on 'Gaslit' when it has been confirmed to me that the entire crew, top to bottom, will be vaccinated."
Nia Tipton is a writer living in Brooklyn. She covers pop culture, social justice issues, and trending topics. Follow her on Instagram.