Five Smartest Villains
We aren't breaking it down by the baddest, the most revered, or the most feared. We're breaking it down by smarts. These five movie villains got to where they were by using their wits and expertise. Since most villains always lose, it's important to note what some of the smartest villains in cinema did to ALMOST beat the heroes.

5. The Joker (Dark Knight)

Heath Ledger's memorable role as the Joker in The Dark Knight  starts our list. This villain's apparent expertise in explosives and his ability to take over Gotham's mob scene make him one of the top five smartest villains in cinematic history.

Within what appears to be a matter of weeks, the mysterious clown becomes Gotham's most powerful gangster, all while managing to persuade the city's chief prosecutor, Harvey Dent, to join the dark side. By the time he's taken down by Batman, the Joker manages to throw the city into chaos, rig two boats with explosives, and take over the vast resources of Gotham's top crime syndicates.

4. Anton Chigurh

In one of the most obscure and mysterious roles ever to grace the big screen, Javier Bardem's role as Anton Chigurh in the Cohen Brother's adaptation of No Country For Old Men  is one of the most frighteningly memorable.

Chigurh is hired by a Mexican drug cartel to track down stolen cash....and track it down he does....with a scary level of precision. Anton Chigurh is one of the few movie villains to beat the hero and walk away a winner. Chigurh tracks down the loot and kills everyone in his path by the end of the movie. If it weren't for other brilliant villains, Chigurh would take the number one spot.
3. John Doe

In David Fincher's 1995 film Seven, Kevin Spacey takes on the role of a brilliant serial killer who kills his victims following a familiar pattern. Through the film, the killer known as John Doe kills seven people who all have one thing in common: they are sinners.

What makes John Doe one of cinema's smartest villains is the perfect execution of his plan, which involves getting caught, murdering the wife of one of the film's protagonists, and then being killed by the said protagonist. At no point in cinematic history (except in another Kevin Spacey movie, The Usual Suspects) has a villain so brilliantly succeeded at besting the hero.

2. Alex DeLarge

In Stanley Kubrick's masterpiece A Clockwork Orange, the main antagonist/protagonist manages to reign supreme over his little clique of droogs and then survive a stint in prison whilst pretending to come out reformed.

What makes DeLarge one of the smartest villains is his ability to convince doctors that he was "cured" by the bizarre and heinous treatments prescribed to him while in prison. Since DeLarge was a depraved rapist to begin with, the question of whether being forced to watch depraved acts on film had any affect on him is still open for debate. His intelligence can be questioned by his complete lack of regard and his inability to avoid being caught in the first place, but, throughout the film, we never really know if Alex DeLarge has any regrets. DeLarge's brilliance lies in his ability to commit a gruesome raping spree while facing only a small punishment. Who but a brilliant sociopath could get away with raping and murdering innocent people by weaseling his way out of a long prison sentence?

1. Emperor Palpatine

Unlike other Star Wars  villains such as Darth Vader and Kylo Ren, Emperor Palpatine doesn't let his emotions get the best of him. It was Darth Vader's emotions that led to his demise and will likely be Kylo Ren's fatal flaw as well (if he isn't a double agent tasked with bringing down the First Order), but Palpatine is different.

If Palpatine were a real world leader and not just a fictional portrayal, we'd all be dead. Palpatine managed to survive six Star Wars  films before being killed. This, for any film franchise villain, is a remarkable achievement. Palpatine rose through the ranks of the Senate to become Supreme Chancellor of the Galactic Republic and then Emperor. Even after being brutally maimed, Palpatine managed to keep a grip on his power. His absolute evil and remarkable achievements make him cinema's smartest and most successful villain of all time.
        August 2016 | Augustus

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