Almost Infamous: 10 Biopics With Memorable Antiheroes

Including films about a serial killer, a mob informant and a computer genius

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Columbia Pictures

Here’s something you might have missed: this past weekend, Benedict Cumberbatch hit screens nationwide as WikiLeaks founder Julian Assange in Bill Condon’s much maligned biopic, The Fifth Estate. Given the media’s incriminating portrayal of Assange, it’s not very surprising that the film was virtually ignored by audiences who opted for astronauts, telekinetic psychopaths and seafaring captains instead.

It’s hard to sell an antihero; it’s even harder to sell one that’s been living in the headlines. The finicky public heads to cinemas to escape reality, not encounter it, so it’s really up to the filmmakers to turn the papers into an extraordinary, must-see event. For further proof, take a look at these 10 solid examples. Love ’em or hate ’em, plenty of popcorn was had in the company of these real-life antiheroes.

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10. Monster (2003) 

Aileen Wuornos (Charlize Theron)

Director Patty Jenkins’ sordid retelling of the late serial killer Aileen Wuornos is gritty and harrowing enough to leave you reaching for hand sanitizer and a bottle of bleach. Theron plays the troubled Wuornos, a Floridian prostitute whose life gets turned astray after she murders a sadistic client of hers. Although she tries to quit this life, she soon has trouble supporting herself and her lover (Christina Ricci), leaving her no choice but to return to her profession. One by one, she starts offing clients, which leads to her ultimate demise. The whole thing plays out like a warped, X-rated version of Thelma & Louise — with an even more depressing ending.

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9. Sid and Nancy (1986)  

Sid Vicious and Nancy Spungen (Gary Oldman and Chloe Webb)

One’s a heroin addict, the other’s a bassist for a legendary band. Together, they’re an irresistible couple that continues to live on in the eyes of every teenager who’s just heard the Sex Pistols. On paper, Sid Vicious and Nancy Spungen’s iconic relationship reads like a punk-rock remake of Samson and Delilah, featuring characters too reckless to be alone and too dangerous to be together. Onscreen, their conjoined downward spiral into addiction still registers as a romantically horrifying cautionary tale worth obsessing over, no thanks to Oldman’s outstanding performance as Vicious. Of course, not everyone was charmed. In his autobiography, Pistols front man and resident grouch John Lydon wrote, “To me, this movie is the lowest form of life.” Oh, well.

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8. Blow (2001)

George Jung (Johnny Depp)

Never heard of George Jung? The full title of the book on which director Ted Demme based his cocaine epic describes him to perfection: Blow: How a Small Town Boy Made $100 Million With the Medellín Cocaine Cartel and Lost It All. Maybe it’s the film’s soundtrack — Rolling Stones, Manfred Mann’s Earth Band, Ram Jam and Cream — but Jung’s unbelievable life in crime is made to seem alluring, sexy and glamorous. It helps that the film stars heartthrob Johnny Depp and Vogue cover all-star Penélope Cruz, who both look stylish all throughout the film, even as the FBI raids their parties or throws handcuffs on them. The joyride comes to a sobering conclusion, however, and it’s one that shuts down the heart for good.

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7. Dog Day Afternoon (1975)

John Wojtowicz (Al Pacino)

How many times have you screamed “Attica!” in jest? Thank screenwriter Frank Pierson. Or Sidney Lumet. Or Al Pacino. Either one’s responsible in this intense, gripping depiction of John Wojtowicz and Salvatore Naturale’s Brooklyn bank robbery in the summer of 1972. Pierson based his Academy Award–winning screenplay around P.F. Kluge’s Life magazine article, “The Boys in the Bank,” changing Wojtowicz’s name to Sonny Wortzik and fudging a few other historical details. What’s still remarkable about the film decades later is Pacino’s sweaty conviction and friendly New York demeanor, two hallmarks that would change bank-heist films forever.

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6. To Die For (1995)

Pamela Smart (Nicole Kidman)

She’s the all-American girl — with a psychotic side. Nicole Kidman’s Golden Globe–winning performance as the sinister wife-turned-sociopath Suzanne Stone is as hilarious as it is terrifying. However, it’s only fun and games until you discover that Gus Van Sant’s obscure mockumentary is actually based on the real-life convicted murderer Pamela Smart. Currently, Smart is serving a life sentence in prison (without parole, no less) for conspiring with her 15-year-old lover and his three friends to kill her husband. It’s a messy story that made waves in the ’90s, but with just the right direction, a spry score by Danny Elfman, and motivated performances in Joaquin Phoenix and Matt Dillon? A strangely entertaining film.

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5. Bonnie and Clyde (1967)

Clyde Barrow and Bonnie Parker (Warren Beatty and Faye Dunaway)

It’s a nice slice of irony when a film about two of America’s most notorious criminals is one of the first 100 films selected for preservation by the U.S. National Film Registry. Then again, the bloody tale of Depression-era gangsters Clyde Barrow and Bonnie Parker is simply irresistible. At the time of its release, Arthur Penn’s crime epic shattered the confines of American cinema, proving that it was O.K. to present sex and violence as either art or something entertaining. Today, however, the film is best known for its performances by Warren Beatty and Faye Dunaway. And c’mon, who could hate a gangster with those faces?

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4. Goodfellas (1990)

Henry Hill (Ray Liotta)

A criminal, addict and mob rat — the late Henry Hill wasn’t much of a hero. Yet that bloodstained résumé hasn’t stopped anyone from sitting down on the couch and tuning into Goodfellas whenever it’s on television. Why? Ray Liotta injects so much character into the film; from his matter-of-fact narration to his obscene outbursts at Lorraine Bracco, Robert De Niro and Joe Pesci. He’s a psychopath surrounded by other psychopaths. Here’s a guy who brings down the Lucchese crime family by lying through his cocaine-stained teeth — and we’re still rooting for him? Either something’s wrong with us mentally (likely) or Martin Scorsese’s just that rare genius who can turn any zero into everyone’s hero (very likely).

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3. The Social Network (2010)

Mark Zuckerberg (Jesse Eisenberg)

It’s hard to applaud Mark Zuckerberg after watching David Fincher’s Oscar-nominated biopic, The Social Network. Jesse Eisenberg plays the role with such weaselly intelligence that it’s less about fanaticism and more about intrigue. As he maniacally evolves Facebook, audiences are left to just stare in disbelief, knowing that their everyday online social tools were created with such ease and amid so much drama. The ensuing legal proceedings between Zuckerberg and Eduardo Saverin (Andrew Garfield) are about as biting and awkward as any Ricky Gervais–led comedy. Screenwriter Aaron Sorkin makes every character just as witty as ol’ Zucks, which adds to the film’s breakneck pace. The film loses steam in the final act, but by then, it’s a strange comedown that leaves you feeling some sympathy for the lonely genius.

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2. American Gangster (2007)

Frank Lucas (Denzel Washington)

Frank Lucas is such an antihero that he inspired an entire album by Jay Z. The North Carolina–born, Harlem-raised gangster made it into history books by smuggling heroin into the States through American service plans during Vietnam. Ridley Scott’s gripping biopic features some of Denzel Washington’s strongest acting to date. The veteran actor captures Lucas’ intelligence and intensity in each scene, even thwarting a solid performance by Russell Crowe, who plays Detective Richie Roberts, a.k.a. the man who nabbed Lucas. Five minutes into the film, you’re both terrified and enthralled by Washington’s vision of Lucas, and even as the cell doors slam shut at the end, there’s little regret in whom you were rooting for.

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1. Raging Bull (1980)

Jake LaMotta (Robert De Niro)

Fact: Martin Scorsese should have won Best Director for Raging Bull. One of the Academy’s most unforgiving oversights continues to precede the director’s seminal 1980 masterpiece about Italian-American middleweight boxer Jake LaMotta. (It helps a bit that statuettes went to Robert De Niro and film editor Thelma Schoonmaker.) As the title suggests, LaMotta is a mythical beast, a force of nature too malevolent to ignore. His relationship with just about everyone onscreen ends in tragedy, but he’s still worth cheering on and losing hope over. Why? Blame it on flawless direction or unprecedented acting, but man, it’s rough rooting here.

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