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It’s undeniable that there’s no one quite like Charlie Sheen, and when Ashton Kutcher stepped in to fill his shoes onTwo and a Half Men, the results were less than stellar. But over the years, Kutcher has found himself in his own fair share of controversies, arguably rivaling Sheen’s infamous reputation.

Most recently, his involvement with Diddy has reignited scrutiny. Here’s a look at other moments when Ashton Kutcher stirred up Hollywood drama and proved to be just as “controversial” as Sheen, if not more so.
1Defending Convicted R-pist Danny Masterson
Funny howAshton Kutcherwent from replacing one controversial star to racking up his own set of scandals. Themost infamous? His defense of Danny Masterson.
In 2023, Kutcher and his wife,Mila Kunis, faced backlash after writing character letters supporting Masterson ahead of his sentencing for r*pe convictions where they describes him as a“role model”and“kind.”(viaVariety)

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Masterson is now serving 30 years to life in prison (viaBBC). Unsurprisingly, the move backfired, leaving Kutcher’s reputation with damage that’s hard to come back from.
2Demi Moore’s Explosive Accusations
Many are aware that Ashton Kutcher and his ex-wifeDemi Moorehad a troubled marriage, but more revelations surfaced when Moore wrote her memoir,Inside Out. In the book, she detailed all the alleged ways Kutcher behaved during their marriage and how he treated her.
Moore claims (viaEW) he was less and less present as a husband, regularly cheated on her, and pressured her into s-x acts she wasn’t comfortable with while she“went into contortions to try to fit the mold of the woman he wanted his wife to be”, including threesomes. She also alleges that he was unsupportive of her sobriety and unapologetic about his bad behavior.

3Ashton Kutcher Was Allegedly A Regular at Diddy’s Infamous Parties
Last but not least is Ashton Kutcher’sconnection to Sean Combs, a relationship that has now raised eyebrows. Combs was arrested in September 2024 on serious charges, including s-x trafficking and racketeering.
“Demi is a s*xually conservative person”: Demi Moore Could Never be a Part of P Diddy’s Freakoffs Despite Ashton Kutcher’s Relationship With the Rapper
His notorious“White Parties”andwild“freak-offs”have long been the stuff of legend, with many come forward now and detailing the outrageous happenings at these events.
Kutcher’s link to the scandal stems from Diddy’s own words, and he once admitted that he, Kutcher, and Jamie Foxx regularly partied together (viaTime). In fact, Kutcher even co-hosted one of Diddy’s infamous White Parties in 2009, showing he was very much part of the scene.

Sampurna Banerjee
Articles Published :1803
Sampurna Banerjee is an Entertainment Writer at FandomWire, and she’s written over 1,700 articles! She covers everything from celebrity news to the latest superhero buzz, streaming shows, and fan theories. If it’s trending in pop culture, Sampurna’s probably already on it.When she’s not working, you’ll probably find her rewatching The Office (again), getting into debates about Marvel’s timeline, or diving deep into Christopher Nolan movies for the hundredth time. She’s not just writing about entertainment, she’s living it.
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Ashton Kutcherdanny mastersonDemi MooreDiddyMila Kunis
