It has been 50 years since history’s most infamous cult leader Charles Manson was convicted of murder for instigating and directing his followers, the Manson Family, to commit the gruesome 1969 Tate-LaBianca crime spree that left seven people — including pregnant rising starlet Sharon Tate — dead. Neither four decades in prison nor his death in 2017 have done much to quell the seemingly universal fascination with the enigmatic madman with mommy issues.

Hollywood seems especially drawn to Manson, his cult, and their crimes. Studios, networks, and streaming services continue to churn out movies, television shows, and documentaries, including the latest, EPIX’s "Helter Skelter: An American Myth."

As a six-episode docuseries, it didn’t need to cast a Charlie, but over the years plenty of fictionalized dramas and parodies, like "Once Upon a Time… In Hollywood," "American Horror Story" and "South Park," have cast the role. Actors jump at the chance to slide into the denim, glue on a beard, and perfect that sinister stare to be a part of the cult programming. In fact, it’s such a killer part that two actors took on the role twice. 

 

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Steve Railsback: "Helter Skelter" (1976)

 

 

You never forget your first, especially when it’s as intense and spot-on as Railsback’s performance in the two-night CBS miniseries based on Vincent Bugliosi’s nonfiction bestseller. He had the added pressure that the crimes and the court case were still fresh in viewers’ minds. It was the highest-rated telefilm until "Roots" aired the following year. Railsback went on to portray another schizophrenic serial killer in 2000’s "Ed Gein." 

 

Michael Reid MacKay: "Summer Dreams: The Story of the Beach Boys" (1990)

 

More than anything, Manson wanted to become a famous musician, and, when Beach Boys drummer Dennis Wilson gave one of his girls a ride in Malibu, he saw a chance. In the summer of ’68, the Manson Family moved into Wilson’s home, dropped acid, and staged orgies. However, they went their separate ways after Manson pulled a knife on Wilson’s producers in the studio.

The Beach Boys recorded an altered version of the cult leader’s song “Cease To Exist,” which they renamed “Never Learn Not To Love." This unauthorized band biopic covered this sinful summer. (Go to the three-minute mark to see MacKay as the prophet.)

 

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Bob Odenkirk: "The Ben Stiller Show" (1992)

 

 

Call him Man(son)'s best friend. Before Odenkirk broke bad with Walter White, the "Better Call Saul" Emmy winner starred in a weird "Lassie" parody on the cult classic sketch show in which the gruesome guru was reimagined as the family dog of a '50s family. When little Timmy gets hurt, Manson's sent to get help. But instead of a warning bark, his psychobabble must be interpreted by Timmy's parents.

 

Marcelo Games: "The Manson Family" (1997)

 

Director Jim Van Bebber’s film recreates the Manson Family’s descent into sex, drugs, madness, and murder through faked home movies and faux news clips. This overly indie film wasn’t released in the U.S. until 2004. 

 

Trey Parker: "South Park" (1998)

 

 

Manson makes a cameo in an episode all the way back in season 2. While Kyle, Stan, and Kenny are in Nebraska to spend the holidays with Eric’s family, Manson escapes from prison with Eric’s uncle, and the boys try to teach him the true meaning of Christmas. He even breaks into a song.

 

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Jeremy Davies: "Helter Skelter" (2004)

 

CBS remade its hit miniseries and hired Davies, the usually soft-spoken "Lost" and "Saving Private Ryan" alumnus, to try to outshine the gold standard, Railsback. This version shifted the plot away from Bugliosi‘s viewpoint to make it more about Manson, Linda Kasabian (Clea DuVall), and the bloody depictions of the murders. 

 

Ryan Kiser: "Lie" (2009) and "House Of Manson" (2014)

 

Kiser was the first thespian to take on Manson in two different projects. "Lie" was a short film that focused on Manson as a singer-songwriter and the making of his first album, "LIE," with Wilson’s help. "House of Manson" dives further back in the timeline and actually paints Charlie as a good time…at first.

 

Taran Killam: "Saturday Night Live" (2014)

 

No stranger to doing impressions of real people — Killam does wicked parodies of Matthew McConaughey, Brad Pitt, and Donald Trump, to name a few — the longtime cast member embodied late-in-life mohawked Manson after he was back in the news announcing he’d fallen in love and gotten engaged while behind bars with a frequent visitor, 26-year-old Star Burton.

 

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Gethin Anthony: "Aquarius" (2015-2016)

 

 

Manson wasn’t the main character in this two-season cop drama that takes place in Los Angeles in 1967. But he was at the center of detective Sam Hodiak’s missing girl case and, thus, gets a beatdown from David Duchovny. Before playing Renly Baratheon on "Game of Thrones," Anthony captured Manson’s real charm, swagger, and temper but had more leeway given the inspired-by storyline. He told IMDB, “We’ve set the parameters of who he is within our story, and that makes it simpler to get into. Because you’re dealing with the expectations of Charlie within the show as opposed to as a historical figure.”

 

Jeff Ward: "Manson’s Lost Girls" (2016)

 

Yep, there’s even a Lifetime movie about Manson. And we’re pretty sure Ward was wearing eyeliner the whole time.

 

Evan Peters: "American Horror Story: Cult" (2017)

 

Ryan Murphy’s go-to leading man for his horror anthology played a local politician obsessed with Trump, Manson, and other charismatic leaders who used fear, theatrics, and lies to grow a following. Peters has said he spent hours studying interviews and documentaries in order to play six cult leaders. Because this is "American Horror Story," eventually things get weird, and he is possessed by Manson. Manson was also mentioned in another installment, "Hotel," but ultimately didn’t appear at the annual serial killer spirits' dinner because he had not yet died in real life. 

 

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Matt Smith: "Charlie Says" (2019)

 

 

Once again, Smith traveled back in time on screen and, no matter how you felt about controlling, cheating Prince Philip or Robert Mapplethorpe’s controversial kinky art, it is impossible to deny that this is the darkest Smith has ever gone. The movie, from the writer/director of "American PsychoMary Harron, takes place after the murders when the women are in jail. While trying to break them free of his spell, they recount the good times on the ranch when it was “all about love.” Smith appears only in flashbacks and goes from dynamic to unhinged, like when Manson explains the “Helter Skelter” theory

 

Damon Herriman: "Once Upon a Time… In Hollywood" (2019) and "Mindhunter" (2019)

 

 

Herriman became the second member of the two-timer’s club in the same year. It wasn’t so much a career plan as a bizarre coincidence. He'd already landed the Netflix series when his former "Justified" costar Timothy Olyphant suggested him to "Once" director Quentin Tarantino. He didn’t tell Tarantino about his other Chuck gig because he just wanted the chance to audition for him despite it being basically one scene. "Mindhunter" was the heavier lift because it takes place after Manson’s in prison, and he’s further out there mentally. Herriman spent six months devouring all things Manson as research. He told Rolling Stone, 

 

“I watched, read, and listened to everything I could get my hands on. I could definitely see why people were mesmerized by him. If you’re a 5-foot-2 guy in your mid-thirties, and a bunch of beautiful 19-year-old women are hanging on your every word, there’s something magnetic about you.”

 

As meaty as Manson is, Herriman doesn’t think a third time would be a charm: “I’ve peaked with two. I’m happy to go back to nice guys with glasses.” He’s made good on that promise with recent roles in Barry Jenkins' "Underground Railroad" on Amazon and the EPIX series "Perpetual Grace, LTD."

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