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Sean Penn’s Controversies Through the Years: Legal Issues and More on September 14, 2023 at 6:21 pm Us Weekly

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Sean Penn Gareth Cattermole/Getty Images

Sean Penn is no stranger to drama, both on and off the screen.

In addition to his career as an Oscar-winning actor and his relationships with A-listers including Madonna, Robin Wright and Charlize Theron, Penn has made headlines through the years for controversial behavior and comments.

Keep scrolling to for a look back at Penn’s biggest controversies over the years:

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Alleged Abuse of Madonna

Penn was married to the “Queen of Pop” from 1985 to 1989. Madonna first filed for divorce in December 1987 but withdrew the papers two weeks later. In January 1989, she filed for divorce again.

Reports surfaced in 1987 — and again in 1989 — alleging that Penn had physically assaulted Madonna. The musician later shut down the claims in 2015 when she testified on Penn’s behalf amid his defamation lawsuit against director and screenwriter Lee Daniels.

According to court documents obtained by The Hollywood Reporter, Madonna’s statement denied reports that Penn allegedly struck her with a baseball bat in 1987 and physically assaulted her in 1989.

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“While we certainly had more than one heated argument during our marriage, 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’s statement read.

After Penn’s divorce from Madonna, he was later married to Wright from 1996 to 2010 and to Leila George from 2020 to 2022. He and Wright share daughter Dylan, born in 1991, and son Hopper, born in 1993.

Incident With David Wolinski

In 1986, Penn was charged with misdemeanor battery for allegedly assaulting Wolinski, a songwriter best known for his work with the band Rufus, at Helena’s nightclub in Los Angeles. Wolinski claimed that the incident began when Penn accused him of trying to kiss Madonna.

Penn pleaded not guilty to the charge and was sentenced to one year of probation.

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Stint in Jail

In 1987, Penn was arrested for punching Jeffrey Klein, an extra on the set of his film Colors. Penn was already on probation at the time and was sentenced to 60 days in jail for the assault and for reckless driving. He served 33 days of the 60-day sentence.

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Altercation With Photographer

In May 2010, the actor pleaded no contest to a misdemeanor charge stemming from an October 2009 altercation with photographer Frank Mateljan. He was sentenced to perform 300 hours of community service and to undergo 36 hours of anger management counseling.

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Footage of the incident obtained by TMZ showed Penn kicking toward the photographer. “Get out, get out,” Penn said as he kicked.

Lawsuit Against Lee Daniels

Daniels mentioned Penn during a September 2015 interview with The Hollywood Reporter when asked about Terrence Howard’s continued career in show business despite his ex-wife Michelle Ghent obtaining two restraining orders against him for alleged domestic abuse in 2011 and 2013.

“[Terrence] ain’t done nothing different than Marlon Brando or Sean Penn, and all of a sudden he’s some f—king demon,” Daniels claimed during the interview.

In response, Penn sued Daniels for defamation, seeking $10 million in damages. He dropped the lawsuit in May 2016 after Daniels issued a public apology retracting his statement.

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“I am so sorry that I have hurt you, Sean, and I apologize and retract my reckless statements about you. How thoughtless of me. You are someone I consider a friend, a brilliant actor and true Hollywood legend and humanitarian,” Daniels’ statement began.

Daniels also called his previous remarks about Penn “cavalier” and said he made them to “express a view regarding the disparate treatment of men of color in our national conversation.”

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Comments About Masculinity

Penn raised eyebrows for comments he made about masculinity during a January 2022 interview with the British newspaper i.

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“I am in the club that believes that men in American culture have become wildly feminized,” he told the outlet at the time. “I don’t think that being a brute or having insensitivity or disrespect for women is anything to do with masculinity, or ever did. But I don’t think that [in order] to be fair to women, we should become them.”

Later that month, he doubled down on his remarks while speaking with the Independent.

“I think that men have, in my view, become quite feminized. I have these very strong women in my life who do not take masculinity as a sign of oppression toward them,” he said. “There are a lot of, I think, cowardly genes that lead to people surrendering their jeans and putting on a skirt.”

Actress Thandiwe Newton was among those who took issue with Penn’s statements.

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“Dude what are you saying?” she wrote via Twitter in response to the Independent interview. “Like for real? You’re a jibbering fool … you used to be sexy but now you’re just tragic.”

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Comments About Will Smith

More than one year after Will Smith slapped Chris Rock at the Oscars in March 2022, Penn shared his feelings on the incident.

“I don’t know Will Smith. I met him once. He seemed very nice when I met him. He was so f—king good in King Richard,” Penn said during a September 2023 interview with Variety.

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He continued, referencing the jail time he served for punching Klein in 1987: “So, why the f—k did you just spit on yourself and everybody else with this stupid f—king thing? Why did I go to f—king jail for what you just did? And you’re still sitting there? Why are you guys standing and applauding his worst moment as a person?”

Smith, who has since apologized for the incident, was banned from attending Academy of Motion Picture Arts and Sciences events for 10 years for slapping Rock.

Sean Penn is no stranger to drama, both on and off the screen. In addition to his career as an Oscar-winning actor and his relationships with A-listers including Madonna, Robin Wright and Charlize Theron, Penn has made headlines through the years for controversial behavior and comments. Keep scrolling to for a look back at Penn’s 

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White Female Jurors Prominent in Sean “Diddy” Combs’ Federal Trial Pool

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Jury selection for Sean “Diddy” Combs’ federal sex trafficking trial is nearly complete in Manhattan, with a significant portion of the remaining jury pool composed of white women. This trend has drawn attention from legal observers, given the sensitive nature of the charges and the broader cultural context.

Rigorous Vetting Process

Judge Arun Subramanian and attorneys have spent several days questioning nearly 100 potential jurors about their experiences with sexual assault, their views on Combs, and their ability to remain impartial despite heavy media coverage. Many jurors referenced the widely circulated hotel surveillance video and expressed strong opinions, leading to multiple dismissals for bias or personal reasons.

Demographic Dynamics

While the court has not released an official demographic breakdown, reports highlight the prominence of white women among those still being considered for the final jury. This has sparked discussion about how the jury’s composition could influence deliberations, especially in a case involving race, gender, and celebrity.

Legal and Social Implications

The jury’s makeup is particularly significant in a case centered on allegations of sexual exploitation. Both sides have been strategic in their questioning, seeking to identify and eliminate potential biases that could affect the outcome.

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Next Steps

Jury selection is expected to conclude by week’s end, with opening statements scheduled for May 12. Combs, who has pleaded not guilty, faces the possibility of a life sentence if convicted. The trial is expected to last up to two months, with national attention focused on both the proceedings and the jury’s verdict.

Bolanle Media covers a wide range of topics, including film, technology, and culture. Our team creates easy-to-understand articles and news pieces that keep readers informed about the latest trends and events. If you’re looking for press coverage or want to share your story with a wider audience, we’d love to hear from you! Contact us today to discuss how we can help bring your news to life

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How the Asian Community is Responding to ‘Sinners’

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How the Asian Community is Responding to ‘Sinners’

Ryan Coogler’s Sinners has become a focal point for conversation within the Asian community, inspiring both pride and critique regarding its depiction of Chinese American characters and their nuanced place in the American South’s racial history.

Historical Visibility and Cultural Depth

Many Asian American viewers have praised Sinners for authentically portraying the little-known history of Chinese immigrants in the Mississippi Delta during the Jim Crow era. The film’s depiction of Asian-owned stores serving both Black and white communities resonates with those who see their own family histories reflected on screen.  The inclusion of cultural details, such as traditional dance and references to Sun Wukong, the Monkey King, has been celebrated as a sign of thoughtful and authentic representation.

“Ryan Coogler didn’t include the Delta Chinese in Sinners as a cool and quirky detail-he made their presence meaningful and grounded it in actual history.”

Controversy and the “Grace Scene”

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The character Grace Chow has become a lightning rod for debate. On social media and forums, some Asian viewers express frustration, feeling that Grace’s actions-interpreted by some as self-preserving at the expense of others-reinforce negative stereotypes about Asians lacking solidarity with other marginalized groups. Viral commentary ranges from disappointment (“Why would you do that? You’re making us look bad out here, Grace!”) to deeper critiques about Asian proximity to whiteness and historical patterns of assimilation..

Others defend Grace’s actions as those of a desperate mother trying to protect her daughter, arguing that her choices reflect the complex, often painful realities faced by immigrants navigating survival in a racially stratified society. This division highlights ongoing debates within the Asian community about identity, loyalty, and the pressures of being caught between Black and white America.

Solidarity, Tension, and Real-World Parallels

The film’s exploration of Asian-Black relations has prompted both praise and critique. Some Asian Americans appreciate the acknowledgment of historical solidarity between the two communities, especially during the civil rights movement. Others note that the film has surfaced unresolved tensions, with some online commentary accusing Asian Americans of benefiting from Black struggle while failing to reciprocate support. These discussions reflect broader societal debates about race, privilege, and allyship.

Celebration and Critique of Representation

Despite controversy, many Asian viewers have lauded Sinners for its cultural richness and multidimensional characters. The film’s willingness to depict Asian Americans as complex individuals-neither model minorities nor mere plot devices-has struck a chord with those seeking more authentic representation in Hollywood. The dance scene featuring Grace and Bo, in particular, has been described as “profoundly touching” and emblematic of the film’s commitment to cultural nuance.

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Yet, there is also critical discussion about how few AAPI characters are written into power dynamics, and how these portrayals can affect audience empathy or reinforce harmful tropes if not shaped by lived experience or community accountability.

Conclusion

The Asian community’s response to Sinners is diverse and passionate. While the film is celebrated for its historical accuracy, cultural detail, and willingness to tackle difficult questions, it has also sparked heated debate about representation, solidarity, and the burdens of visibility. Ultimately, Sinners has succeeded in prompting a vital conversation-one that reflects both the diversity and dynamism of Asian American perspectives today..


Bolanle Media covers a wide range of topics, including film, technology, and culture. Our team creates easy-to-understand articles and news pieces that keep readers informed about the latest trends and events. If you’re looking for press coverage or want to share your story with a wider audience, we’d love to hear from you! Contact us today to discuss how we can help bring your news to life

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Tyler Perry Studios and Courtney Glaudé Shine Spotlight on Dementia with “Old Gray Mare”

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Tyler Perry Studios presented an exclusive screening of Old Gray Mare, a poignant short film by writer-director Courtney Glaudé, at the 49th annual Atlanta Film Festival (ATLFF) on April 27, 2025. The screening, held at the historic Plaza Theatre’s LeFont Auditorium, drew a packed house eager to experience Glaudé’s latest work, which tackles the emotional realities of dementia-a subject affecting millions of families across the globe.

Dexter Walker & Courtney Glaude at ATLFF2025

Old Gray Mare follows Steven and Robin as they visit Eileen after returning from a cruise, only to find themselves confronting the devastating impact of memory loss. What begins as typical forgetfulness soon spirals into something far more alarming, forcing the characters-and viewers-to grapple with the painful progression of dementia. The story’s authenticity is heightened by a talented cast including Charnele Brown, Devale Ellis, Larissa Dali, and Tyler Lepley, with Glaudé himself producing alongside Antoinetta Stallings and Gracie Henley.

The film’s 28-minute runtime delivers a powerful emotional punch, blending sensitive storytelling with striking visuals by cinematographer Gracie Henley and editing by Stanley Hillard Jr. The screening was followed by a panel featuring Glaudé, cast members, and Antoinetta Stallings, VP of Development & Acquisitions at Tyler Perry Studios. The discussion offered insights into the making of the film and highlighted Tyler Perry Studios’ ongoing commitment to telling impactful, socially relevant stories.

The event underscored ATLFF’s reputation as a platform for diverse voices and compelling narratives, further solidifying the festival’s role in connecting audiences with filmmakers who are unafraid to tackle challenging subjects.


Walker & Devale Ellis at the ATLFF 2025

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Bolanle Media covers a wide range of topics, including film, technology, and culture. Our team creates easy-to-understand articles and news pieces that keep readers informed about the latest trends and events. If you’re looking for press coverage or want to share your story with a wider audience, we’d love to hear from you! Contact us today to discuss how we can help bring your news to life

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