10 Greatest Pop-Culture Devils of All Time

Tonight marks the debut of the CW’s Kevin Smith–directed, Vulture-approved comedy Reaper, in which a 21-year-old slacker (Bret Harrison) finds out that his parents sold his soul to the devil (Ray Wise) before he was born. On the show, Wise does admirable work as the Prince of Darkness, but his is just the latest in a long line of top-notch TV and movie Satans. When our Kid Nation coverage inevitably earns both of your Vulture editors a permanent vacation in the fiery pits of hell, who would we most like to see in charge? Here’s our list of the Ten Greatest Pop-Culture Devils of All Time.

10. Ray Wise in Reaper (2007)
As the dapper, devil-may-care Devil in Reaper, Ray Wise — formerly of 24 — is a deadpan lord of the underworld, but when his anger boils over, watch out.

9. Peter Cook in Bedazzled (1967)
As breezy George Spiggott, the Devil that bedevils Dudley Moore’s Faustian Stanley Moon in this Swinging London classic, Cook is Ray Wise’s soft-spoken predecessor. “There was a time when I used to get lots of ideas,� he muses. “I thought up the Seven Deadly Sins in one afternoon. The only thing I’ve come up with recently is advertising.�

8. Dave Grohl in Tenacious D in: The Pick of Destiny (2006)
The idea of Nirvana’s beatkeeper as the hard-rocking eternal punisher of unrepentant souls certainly sounds awesome, right? If you’re one of the 27 people who actually saw this film in a theater, perhaps you can let us know!

7. The Robot Devil in Futurama (1999-2003)
Played by Dan Castellaneta, this stainless-steel Beelzebub shines in Futurama’s final episode, “The Devil’s Hands Are Idle Playthings,� in which he switches hands with Fry and utters the memorable lament, “Give me back my hands! These things are always touching me in … places.�

6. Billy Crystal in Deconstructing Harry (1997)
Prior to his appointment as the Lord of the Darkness in Woody Allen’s dirtiest-ever film, Crystal’s Lucifer was the head of a major film studio. Still, we’re pretty sure we could count on him to make our stay in hell more comfortable — he even has an air conditioner because “it fucks up the ozone layer.�

5. Robert De Niro in Angel Heart (1987)
In one of the least surprising spoilers in history (p.s. SPOILER ALERT!!!), Lou Cyphre (get it? Lou Cyphre? LouCyphre? LUCIFER!) turns out to be Satan himself, played here as a preternaturally calm, ponytailed, hard-boiled-egg-eating man with really long fingernails, who stole the soul of forties-era crooner Johnny Favorite (Mickey Rourke). De Niro reportedly based the performance on an impersonation of Martin Scorsese.

4. Jack Nicholson in The Witches of Eastwick (1987)
In this adaptation of Updike’s novel, Nicholson plays rich, horny, Devil-incarnate Daryl Van Horne who uses his evil powers to score with three much younger women, all in the span of just 118 minutes. His performance was reportedly based on what he does on one of his more typical Tuesday nights.

3. Satan in South Park: Bigger, Longer and Uncut (1999)
Trey Parker and Matt Stone’s great movie musical refuses to make Satan the villain; instead, he’s the dignified but abused lover of a recently killed Saddam Hussein. “How come you always want to make love to me from behind? Is it because you want to pretend I’m somebody else?� he asks, to which Saddam replies, “Satan, your ass is gigantic and red. Who am I going to pretend you are, Liza Minnelli?�

2. Jon Lovitz in Saturday Night Live (1985–1990)
In his most memorable appearance as the ludicrously red-suited Mephistopheles, Lovitz took a breach of contract case to the People’s Court. The sketch is made by Lovitz’s straight-faced indignance in the face of daunting odds. “Now, you listen to me, I’m Mephistopheles, Prince of Darkness!� he shouts. “When I start harassing you, you’ll know it!�

1. Al Pacino in The Devil’s Advocate (1997)
The movie didn’t really live up to its potential as the Firm-Exorcist hybrid it was pitched as, but Pacino’s scenery-chewing performance as John Milton, the Manhattan attorney who just happens to be the Prince of Darkness, ranks among his personal best, and renders his entire supporting cast (including Keanu Reeves as a block of wood) pretty much inert. “I’m maybe the last humanist,� he barks at one point. “The twentieth century was entirely mine. I’m peaking!�

(Note: If you think we forgot Damn Yankees’s Ray Walston, you’re wrong — he wasn’t considered because we love the Yankees and therefore find film’s title both vulgar and offensive.)