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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.

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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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Advice

How Far Would You Go to Book Your Dream Role?

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The question Sydney Sweeney’s career forces every serious artist to ask themselves.


Most people say they want to be an actor. But wanting the life and being willing to do what the life requires are two entirely different things. Sydney Sweeney’s performance as Cassie Howard in Euphoria is one of the clearest examples in recent television of what it actually looks like when an artist refuses to protect themselves from the story they are telling.


The Performance That Started a Conversation

Cassie Howard is not a comfortable character to watch. She is messy, desperate, and heartbreakingly human in ways that most scripts would have softened or simplified. Sydney Sweeney did not soften her. She played every scene at full exposure — the breakdowns, the humiliation, the moments where Cassie is both completely wrong and completely understandable at the same time.

What made the performance remarkable was not the difficulty of the scenes. It was the consistency of her commitment to them. Night after night on set, take after take, she showed up and gave the camera something real. That is not a small thing. That is the kind of discipline that separates working actors from generational ones.

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What the Industry Does Not Tell You

The entertainment industry sells you a version of success built around talent, timing, and luck. And while all three matter, none of them are the real differentiator in a room full of equally talented people. The real differentiator is willingness — the willingness to be honest, to be vulnerable, and to let the work require something personal from you.

Most actors hit a wall at some point in their career where a role demands more than they have publicly shown before. The ones who say yes to that moment, who trust the material and the director enough to go somewhere uncomfortable, are the ones audiences remember long after the credits roll.

Sydney Sweeney said yes repeatedly. And the industry took notice.


The Question Worth Asking Yourself

Before you answer, really think about it. There is a moment in every serious audition room where someone might ask you to go further than you are comfortable with — to access something real, to stop performing and start revealing. In that moment, you have to decide what your dream is actually worth to you and, more importantly, what parts of yourself you are not willing to trade for it.

That is the question Euphoria quietly raises for anyone watching with ambition in their chest. Not “could I do that,” but “should I ever feel pressured to.” There is a difference between an artist who chooses vulnerability as a creative tool and one who is pressured into exposure they never agreed to. Knowing that difference is not a weakness. It is the most important thing a young actor can understand before they walk into a room that will test it.

Because the only role that truly costs too much is the one that asks you to abandon who you are to play it.

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What You Can Take From This

Whether you are an actor, a filmmaker, a content creator, or someone simply building something from scratch, the principle is the same. The work that connects with people is almost always the work that cost the creator something real. Audiences can feel the difference between performance and truth. They always could.

Sydney Sweeney did not become one of the most talked-about actresses of her generation because she got lucky. She got there because she was willing to be completely, uncomfortably human in front of a camera — and because she knew exactly who she was before she let the role take over.

That combination — full commitment and a clear sense of self — is rarer than talent. And it is the thing worth chasing.


Written for Bolanle Media | Entertainment. Culture. Conversation.


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Entertainment

Bieber’s Coachella Set Has Everyone Arguing Again

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And honestly? That might be exactly what he wanted.

Justin Bieber stepped onto the Coachella stage Saturday night as the highest-paid headliner in the festival’s history — reportedly pocketing $10 million — and proceeded to sit down at a laptop and play YouTube videos.

The internet, predictably, lost its mind.


What Actually Happened

This was Bieber’s first major U.S. performance since his Justice era — a long-awaited comeback after battling Ramsay Hunt syndrome in 2022, which caused partial facial paralysis, plus years of mental health struggles and a very public disappearing act from the industry.

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The stage setup was minimal: a fluid cocoon-like structure, no backup dancers, no elaborate lighting rigs. Just Bieber, a stool, and a laptop.

He opened with tracks from his 2025 albums Swag and Swag II, then invited the crowd on a journey — “How far back do you go?”

What followed was a nostalgic scroll through his entire career: old YouTube covers before he was famous, classic hits Baby and Never Say Never playing on screen while he sang alongside his younger self. Guests including The Kid Laroi, Wizkid, and Tems joined him throughout the night.

He even played his viral “Standing on Business” paparazzi rant and re-enacted it live, hoodie on, completely unbothered.

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The Moment Nobody Predicted

But here’s what the critics burying him in their hot takes chose not to lead with: Bieber closed his set with worship music.

In the middle of Coachella — one of the most secular stages on the planet — he performed songs rooted in his Christian faith, openly crediting Jesus as the reason he was standing on that stage at all.

It wasn’t subtle. It wasn’t a quick prayer and a thank-you. He leaned into it fully, in front of a crowd of 125,000 people who came expecting pop bangers and got a testimony instead.

For fans who have followed his faith journey — his deep involvement with Hillsong and later Churchome, his baptism in 2014, and his very public declaration that Jesus saved his life during his darkest years — the moment landed like a full-circle miracle.


Why People Are Mad

Critics have been brutal.

Zara Larsson summed up the skeptics perfectly, posting on TikTok: It’s giving let’s smoke and watch YouTube — and that clip went just as viral as the performance itself.

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One fan on X wrote: I’m crying, this might actually be the worst performance I’ve ever seen. He’s just playing videos from YouTube… zero effort, pure laziness.”

The comparison to Sabrina Carpenter’s Friday headlining set — elaborate staging, multiple costume changes, celebrity cameos — only made Bieber’s stripped-down show look more controversial.

And the $10 million figure kept coming up. People felt cheated.


Why His Fans Think Everyone’s Missing the Point

Here’s where it gets interesting.

One commenter on X put it best: “He did not force a high-production machine that could burn him out again. Instead, he sat with his past, scrolling through old YouTube videos, duetting with his younger self, and mixing nostalgia with new chapters.”

As the set progressed, Bieber visibly opened up. He removed his sunglasses. He took off his hoodie. He smiled, made jokes about falling through a stage as a teenager.

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One Instagram account with millions of followers posted: This Justin Bieber performance healed something in me.”

That healing language is intentional for Bieber — it mirrors how he talks about his faith. In interviews, he has repeatedly said Jesus didn’t just save his career; He saved his life. The worship set at Coachella wasn’t a gimmick. It was a confession.

The Hollywood Reporter noted the performance also sparked a broader debate about double standards — whether a female artist could ever get away with the same low-key approach without being completely destroyed.


The Bigger Picture

Love it or hate it, Bieber’s Coachella set is the most talked-about moment from Weekend One — more than Karol G making history as the first Latina to headline the festival, more than Sabrina Carpenter’s spectacle.

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That’s not an accident.

In an era where every headliner tries to out-produce the last one, Bieber walked out with a laptop, a stool, and his faith — and made it personal. For millions of fans watching, the worship songs weren’t filler. They were the point.

Whether you call it lazy or legendary, one thing is clear: Justin Bieber isn’t performing for the critics anymore. He’s performing for an audience of One — and the rest of us just happened to be there.


Drop your take in the comments — was Bieber’s Coachella set lazy, legendary, or something even bigger?

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Entertainment

Vertical Films Changed Everything. Are You Ready?

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People don’t watch films the way they used to—and if you’re still cutting everything for the big screen first, you’re losing the audience that lives in your pocket.

Every swipe on TikTok is a tiny festival: new voices, wild visuals, heartbreak, comedy, and chaos, all judged in under three seconds. In that world, vertical films aren’t a gimmick. They’re the new front door to your work, your brand, and your career.

The movie theater is now in your hand

Think about where you’ve discovered your favorite clips lately: your phone, in bed, in an Uber, between texts. The “cinema” experience has shrunk into a glowing rectangle we hold inches from our face. That’s intimate. That’s personal. That’s power.

Vertical video fills that space completely. No black bars. No distractions. Just one story, one face, one moment staring back at you. It feels less like “I’m watching a movie” and more like “this is happening to me.” For storytellers, that’s gold.

The old rules still matter—but they bend

Film school taught you:

  • Compose for the wide frame.
  • Let the world breathe at the edges.
  • Save the close-up for maximum impact.

Vertical filmmaking says: bring all of that craft… and then flip it. You still need composition, rhythm, framing, and sound. But now:

  • The close-up is the default, not the climax.
  • Depth replaces width—what’s in front and behind matters more than left and right.
  • Micro-scenes—60 seconds or less—must feel like complete emotional beats.

It’s not “less cinematic.” It’s a different kind of cinematic—one that lives where people already are instead of asking them to come to you.

Your characters can live beyond the film

Here’s the secret no one tells you: audiences don’t just fall in love with stories; they fall in love with people. Vertical video lets your characters exist outside the runtime.

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Imagine this:

When someone feels like they “know” a character from their feed, buying a ticket or renting your film stops feeling like a risk. It feels like catching up with a friend.

Behind the scenes is no longer optional

Vertical films thrive on honesty. Shaky behind-the-scenes clips. Laughing fits between takes. The director’s 2 a.m. rant about a shot that won’t work. The makeup artist fixing tears after a heavy scene. That’s the texture that makes people care about the final product.

You don’t have to be perfect. You have to be present.
Ideas you can start capturing tomorrow:

  • “What we can’t afford, so we’re faking it.”
  • “The shot we were scared to try.”
  • “One thing we argued about for three days.”

When you show the process, you’re not just selling a film—you’re inviting people into a journey.

Think in episodes, not posts

Most people treat vertical video like a one-off blast: post, pray, forget. Instead, think like a showrunner.

Ask yourself:

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  • If my project were a vertical series, what’s Episode 1? What’s the hook?
  • How can I end each clip with a question, a twist, or a feeling that makes people need the next part?
  • Can I tell one complete emotional story across 10 vertical videos?

Suddenly, your feed isn’t random. It’s a season. People don’t just “like” a video—they “follow” to see what happens next.

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The attention is real. The opportunity is bigger.

We’re in a rare moment where a micro-drama shot on your phone can sit in the same feed as a studio campaign and still win. A fearless 45-second monologue in a bathroom. A quiet scene of someone deleting a text. A single, wordless push-in on a face that tells the whole story.

Vertical films give you:

  • Low cost, high experimentation.
  • Immediate feedback from real viewers.
  • Proof that your story, your voice, your world can hold attention.

You don’t have to wait for permission, a greenlight, or a perfect budget. You can start where you are, with what you have, and let the audience tell you what’s working.

So, are you ready?

Some filmmakers will roll their eyes and call vertical a phase. They’ll keep making beautiful work that no one sees until a festival says it exists. Others will treat every swipe, every scroll, and every tiny screen as a chance to connect, teach, provoke, and move people.

Those are the filmmakers whose names we’ll be hearing in five years.

The question isn’t whether vertical films are “real cinema.” The question is: when the next person scrolls past your work, do they feel nothing—or do they stop, stare, and think, “I need more of this”?

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