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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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Vinnie Zuffante/Michael Ochs Archives/Getty Images

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.

Vinnie Zuffante/Michael Ochs Archives/Getty Images

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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DJ Shinski Brings AfriqueFest To Life

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AfriqueFest: Pan-African Musical Experience — World Cup Edition is set to take over Noto Houston on Sunday, June 28, bringing together East, South, and West African sounds in one immersive celebration of music, culture, and connection. Presented by Experience Noir and Bolanle Media, the event is designed as a cinematic night for the culture, blending global energy with Houston nightlife in a way that feels elevated, intentional, and deeply rooted in African creativity.

Spotlight on DJ Shinski

At the heart of this year’s experience is DJ Shinski. Born and raised in Nairobi, Kenya and now based in Houston, DJ Shinski has built an international name off high-energy sets that move effortlessly across Afrobeats, Amapiano, hip‑hop, dancehall, reggae, and electronic sounds.

He has also become Africa’s most‑subscribed DJ on YouTube, crossing the 2‑million‑subscriber mark and turning his mixes into a global destination for music lovers.

DJ Shinski’s style is precise but unpredictable: one moment it’s classic Afrobeats, the next it’s East African anthems, then a run of throwback hip‑hop or R&B that still feels fresh. That ability to read a room and connect multiple worlds in a single set is exactly why AfriqueFest is building so much of the night’s energy around him.

At AfriqueFest, DJ Shinski helps drive the Safari Grooves segment, representing East and Central Africa from 4 PM to 6 PM. Expect a journey that moves from Nairobi to Dar es Salaam, Kampala, Addis, and beyond, all filtered through his signature “vibes on vibes” approach behind the decks.

DJ Tunez and the rest of the night

Supporting that energy, DJ Tunez leads the Gold Coast Beats chapter from 8 PM to 10 PM, bringing his own Nigerian‑American Afrobeats pedigree to the stage. Together with the Diamond Rhythms segment (South) and a curated roster of DJs, the night stretches across the continent in three distinct musical chapters, all connected by a single dance floor.

Hosted by @chris_gone_crazy, @kingdrewwskyy, @roselynomaka, and @samsnewleaf, AfriqueFest is positioned as more than a party—it’s a celebration of sound, style, and Pan‑African identity in Houston, with DJ Shinski anchoring the experience from the moment doors open.

Brought to you by Bolanle Media & Experience Noir

Brought to you by Bolanle Media and Experience Noir, this World Cup edition of AfriqueFest is crafted as a night where global DJs, storytellers, and music lovers collide and create a shared cultural memory. With DJ Shinski front and center—and DJ Tunez helping close the night—guests can expect a show that reflects both the future of African nightlife and the power of the diaspora to create unforgettable live moments.

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If you want to experience DJ Shinski live at AfriqueFest, now is the time to lock in your spot. Purchase your tickets now at AfriqueFest.com and get ready for a night of music, movement, and culture at Noto Houston.

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STREAMING PREMIERE · JUNE 13, 2026

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Laughter Meets Inspiration: Our Ladies Show Lands on The Roku Channel

A bold new sketch comedy series for women premieres June 13 across the U.S., U.K., and Canada — arriving on the back of a festival-winning run that has critics and audiences already paying attention.

It isn’t every day a brand-new comedy arrives already wearing a row of trophies. Our Ladies Show does. The seven-episode inspirational sketch comedy series — created, written by, and starring Christin Jezak — begins streaming on The Roku Channel on Friday, June 13, 2026, available free to viewers in the United States, United Kingdom, and Canada.

Produced in partnership with global media services leader Encompass Digital Media, the series sets out to do something rare in today’s streaming landscape: make women laugh out loud and leave them lifted. In a media moment crowded with noise and cynicism, Our Ladies Show is a deliberate counterweight — comedy with a conscience, built for women of every age and background.

A Show Built Around Real Life — and Real Laughs

Each of the seven episodes opens with a monologue from one of the cast members introducing the theme, then rolls into three or more sketches that hit the subject from every comedic angle. The series tackles the things women actually carry: holding grudges, comparison, beauty, patience, gift giving, the importance of community, and dealing with anxiety.

The comedy comes from a place of warmth rather than mockery — a “laugh at ourselves” spirit that runs through a gallery of unforgettable characters: a nosey neighbor, an overwhelmed mom, relentlessly optimistic flight attendants, beauty pageant winners past their prime, and a crew of unruly campers with a counselor who simply cannot hold it together.

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Then the show does something most sketch series don’t. In the final segment of every episode, the cast gathers in a living-room setting and invites the audience in — sharing real inspiration drawn from the theme, the sketches, and their own personal stories. It’s the moment the laughter turns into something that stays with you.

The Women Behind the Show

Our Ladies Show brings together three performers with serious range:

  • Christin Jezak — creator, writer, and star (Miracle at Manchester, Raising Hope, Jimmy Kimmel Live!)
  • Hillary Hawkins — (Primal, Nick Jr.’s Play Along, Gullah Gullah Island)
  • Sarah Hernandez — (Nefarious, Unplanned, House of Payne)

“In a world with so much division and depression, I hope women of all ages and backgrounds will watch this show, laugh, be reminded of how beautiful, unique, and loved they are, and remember how much we need each other.”— Christin Jezak, Creator & Star

Already a Festival Favorite

The series’ recurring long-form sketch, Neighborhood Watch, didn’t arrive quietly. Originally released as a web series and revamped for Our Ladies Show with new footage, sound, and music, it has been sweeping the festival circuit:

  • 🏆 Best Webseries — 2026 New Media Film Festival (Los Angeles)
  • 🏆 Best Web/TV Series — Paris Film Awards
  • 🏆 Best Web Series — Dallas Movie Awards
  • 🏅 Additional wins at the London Movie Awards, Florence Film Awards, and Hollywood Gold Awards
  • 🎬 Official Selection — 2026 Harvard Divinity School Film Fest
  • ⭐ Finalist — Houston Comedy Film Festival
  • 📣 Three nominations — 2025 Content Christian Media Conference, including Best Actress in a TV and Web Series nods for both Christin Jezak and Sarah Hernandez

Where and When to Watch

Our Ladies Show premieres Friday, June 13, 2026, streaming on The Roku Channel — the home of premium and free entertainment — in the U.S., U.K., and Canada. All seven episodes deliver the series’ signature blend of sharp sketch comedy and genuine encouragement.

Click Here To Get Tickets

Watch the trailer now on your platform of choice:

For more information, visit www.ourladiesshow.com and follow @ourladiesshow on Facebook, Instagram, and TikTok.


About Christin Jezak

Christin Jezak has worked for over 15 years in the entertainment industry. She created and stars in Our Ladies Show and the award-winning web series Neighborhood Watch. She produced the EWTN TV program For the Sake of the Gospel and the all-women web series Ladies Keepin’ It Real, played Dr. Sam in Miracle at Manchester (starring Dean Cain, Daniel Roebuck, and Eddie McClintock), and voices Agnes in the podcast Confessions of a Catholic Single. She held a lead role in a short film for NTT Data directed by Academy Award–winning cinematographer Janusz Kamiński, has co-starred on Raising Hope, and appeared in Jimmy Kimmel sketches and a Grubhub Super Bowl commercial.

About The Roku Channel

Roku pioneered streaming on TV and is the #1 TV streaming platform in the U.S., Canada, and Mexico by hours streamed (Hypothesis Group, Dec. 2025). The Roku Channel is the home of premium and free entertainment, alongside Roku’s Howdy and Frndly TV services. Roku is headquartered in San Jose, California.

About Encompass Digital Media

Encompass Digital Media is a global managed services company — technology-driven, software-defined, and people-powered. Trusted by world-leading broadcasters, networks, sports rights-holders, and OTT platforms, it processes over 25,000 hours of content daily, serves 850 channels to 84 countries, distributes over 243,000 live events annually, and reaches 400 million radio listeners weekly worldwide. Learn more at www.encompass.tv.

Media & Interview Requests: To interview creator Christin Jezak or the cast, contact Christin at cjezak@p2ptheatre.com.

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What Filmmakers Should Actually Steal From Euphoria

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Most of the talk about Euphoria asks one question: was it realistic? That’s the wrong question if you make films. The better one is simpler. How did Sam Levinson get an audience to feel addiction from the inside? And what did it cost him to end the show the way he did?

Strip away the noise and Euphoria is a clinic in three choices: point of view, style, and the ending. Here’s what’s worth taking — and what isn’t.

1. Put the Camera Inside the Character

Most shows about drugs watch from across the room. Euphoria doesn’t. When Rue is high, the camera is high too. Walls breathe. Floors tilt. Time skips. You’re not watching her — you’re stuck inside her head.

That’s the lesson: point of view is a decision you make with the camera and the cut, not a mood you add later in color. Levinson builds it into the lens, the blocking, and the edit.

So before you shoot a scene through a character’s eyes, ask one thing on set: whose eyes is this lens standing in for? Then make every cut respect that.

2. Your Style Has to Mean Something

The glitter. The slow push-ins. The impossible club lighting. Euphoria‘s look got copied everywhere. That’s the trap.

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The style worked because it carried weight. The beauty wasn’t decoration — it was the lie addiction tells you, the reason the next high looks worth it. The camera made self-destruction gorgeous on purpose.

The copies missed that. A thousand music videos took the look and left the meaning behind, and you can feel how hollow they are. So here’s the test: if your signature style could be swapped onto any other project and still “work,” it’s not a style. It’s a filter. Every choice should have a reason behind it.

3. The Ending Tells the Audience What It All Meant

When Euphoria ended for good in Season 3, Levinson killed Rue — an accidental, fentanyl-laced overdose. He called it “the honest ending,” saying he wanted to tell a true story about addiction and grief in a time when one mistake can be the last one. Reportedly, that wasn’t the original plan; the death of Angus Cloud, who played Fezco, changed the script.

Forget whether you agree with the choice. Study how it works. An ending is the last instruction you give your audience about how to read everything before it.

By ending on consequence instead of recovery, Levinson reframed seven years of beautiful chaos as a story about cost — not a celebration of it.

It’s also the show’s most debatable move, and that’s worth noticing too. A show that spent years making pain look beautiful had to fight to make that pain land as loss. Did it earn the ending, or enjoy the wreckage too long to stick it? Smart filmmakers will disagree — and that argument is exactly what a good ending is supposed to start.

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What Not to Take

The neon grief is the most copied part. It’s also the least useful. Take the surface — the colors, the slow-mo, the trauma-as-texture — and you get the costume without the body.

The real craft is underneath. Commit your camera to a real point of view. Make every stylistic choice earn its place. Treat your ending as the point of the whole thing. Do that, and your work won’t look like Euphoria. It’ll do what Euphoria did.


This piece touches on addiction and substance use. If you or someone you know is struggling, support is available through the SAMHSA National Helpline at 1-800-662-4357.

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