It wasn’t just another red-carpet premiere in Los Angeles on Thursday night—it was a night packed with unexpected reunions and throwbacks to some of Hollywood’s most headline-making stories. Charlie Sheen, once dubbed the “bad boy of Hollywood,” launched his new Netflix docuseries Aka Charlie Sheen, and among those by his side were familiar faces from both his turbulent past and his complicated personal life.
Denise Richards Steps Out Amid Divorce Drama
One of the biggest surprises of the evening was the presence of Sheen’s ex-wife, Denise Richards.
The 54-year-old actress, who is currently navigating a bitter divorce from Aaron Phypers, made a glamorous entrance in a black shimmering crop top paired with sleek silk trousers.
With her signature blonde hair styled straight and parted to the side, Denise easily turned heads.
Her appearance alongside Sheen caught attention, considering their stormy past.
The two married in 2002 and divorced in 2006, sharing two daughters, Sam and Lola.
Their divorce in 2005 was anything but quiet—Richards accused Sheen of violent threats, reckless behavior, and endangering their children.
But time has shifted their dynamic, with Sheen even making a cameo on her reality show Denise Richards & Her Wild Things years later.
A Rare Appearance from Heidi Fleiss
Adding to the evening’s unexpected lineup was Heidi Fleiss, the infamous “Hollywood Madam” who once supplied escorts to Sheen.
At 59, she walked the red carpet in a black coat with tan sleeves, black pants, flip-flops, and her curls bouncing freely.
Though she and Sheen didn’t pose for photos together, Fleiss showed support for her former client by attending the event.
Their history runs deep—Sheen testified at her 1995 trial, admitting he had spent over $53,500 on escorts through her services.
Fleiss, who will soon be portrayed by Aubrey Plaza in a biopic, served 20 months of a seven-year prison sentence for tax evasion.
Interestingly, Fleiss also features in Sheen’s docuseries, where she doesn’t hold back, calling him a “crybaby” and reminding viewers that his testimony helped send her to prison.
Charlie’s Red Carpet Look
While the women drew plenty of attention, Sheen himself kept things classic.
The 60-year-old actor arrived in a dark grey jacket, white button-up, and jeans, finished with black sneakers.
He posed with Denise Richards, proving that whatever wounds existed between them, they’ve at least managed to share a public smile.
Inside the Docuseries: Nothing Off Limits
Aka Charlie Sheen, directed by Andrew Renzi, is set to hit Netflix on September 10.
Billed as raw and unfiltered, the two-part series takes a deep dive into Sheen’s chaotic life—from drug scandals and public meltdowns to his tabloid infamy and career downfall.
In the trailer, Sheen is brutally honest: “When you got a lot of shame about a lot of stuff… shame is suffocating.
I lit the fuse, you know, and my life turns into everything it wasn’t supposed to be.”
The doc features appearances from key people in his life, including Denise Richards, Brooke Mueller (his third ex-wife), Sean Penn, Chuck Lorre, Jon Cryer, Chris Tucker, and his brother Ramón Estévez.
Even his former drug dealer makes an appearance, recalling Sheen’s infamous crack cocaine binges.
A Hollywood Story Still Being Written
From messy divorces to courtroom drama, Sheen’s past has long been an open book.
But this docuseries promises to tell the story in his own words, with contributions from the people who know him best—and in some cases, those who clashed with him the most.
For Sheen, it’s a chance to reclaim his narrative.
For viewers, it’s a reminder that behind the tabloid headlines, there’s a man who burned brightly, fell hard, and is now ready to tell the unfiltered truth.