Face of an Angel, Mind of a Demon

"New rule, Somali pirates have to stop being so darn cute! This is the New York debut of the one surviving member of the apparent boy band that kidnapped that cargo ship, and the new face of evil looks like he's just hoping to see The Lion King!"

- Bill Maher, Real Time with Bill Maher, April 24, 2009.

Most of the time, evil characters will have a stereotypical "evil" look to them. Not these guys. These villains have the looks that are generally associated with absolute innocence. Of course, don't be surprised if they use that to their advantage.

Not to be confused with Beauty Is Bad or Evil Is Sexy, as looking attractive and looking innocent/virtuous are not necessarily associated with each other. (If anything, they are sometimes contrasted.)

Also not to be confused with the Killer Rabbit, who looks weaker than they are, but not necessarily more innocent. Enfant Terribles are often this. Contrast Face of a Thug

Anime and Manga

 * Johan Liebert from Monster has a pleasant, almost angelic face. He is evil incarnate.
 * El Hazard 2 - while Kalia may look sweet and innocent, don't be fooled. In truth, she's
 * Dietrich Von Lohengrin from Trinity Blood. In-universe, he's described as having the face of an angel but the heart of a devil.
 * In Gankutsuou, this is done with Andrea, as is the case in the original The Count of Monte Cristo (see Literature below). While Generic Cuteness is in play, Andrea is still the most Bishonen cast member, and has blond Princess Curls. The only hint of his true nature as a depraved psychopath is the fact that he has rather slitted eyes which reveal themselves as Hellish Pupils when his affable mask drops.
 * Glemmy Toto of Mobile Suit Gundam ZZ is a charming 17-year old with a goofy personality and the face of the bishiest pretty boy you ever did meet. He's a clone of Gihren Zabi, the UC version of Adolf Hitler and is the running for the title of "most evil person in the show".
 * This is said, nearly word-for-word about the recently-deceased daughter of a couple who buy a rabbit from Count D in Pet Shop of Horrors.
 * The minor villain Maurice Cole fits the trope best in Kuroshitsuji (manga), and he wrings every drop of advantage of it. The Villain Protagonist Ciel also does a great job of turning on his charm when it benefits him, but the other end of his range extends through cold and mature to Creepy Child, which doesn't fit this trope so well. Other characters, such as Sebastian, may be extremely beautiful but lack the aura of innocence.

Comic Books

 * One such character named Angelface (guess what he looks like) appears in a Blueberry story, as part of a plot to kill Lincoln. He ends up getting his face shoved into a locomotive's furnace
 * Word of God says that Kroenen from Hellboy literally was a choir boy before he became a self-mutilating psychopathic Nazi ninja zombie.

Film

 * The actor chosen to play the Scorpio Killer (pictured above) from Dirty Harry was chosen because he had a "face like a choir boy." Scorpio is a murdering psychopath and a Complete Monster.

Literature

 * Played (sort of) straight in Discworld with Mr. Teatime from Hogfather, since his eyes serve as a Red Right Hand.
 * Played completely straight by Carcer in Night Watch, who could be standing in the middle of a room full of bloody corpses with a knife in his hand and say "What, me?" while looking genuinly hurt by the accusation.
 * Ferahgo the Assassin from Salamandastron has baby blue eyes which make him look completely innocent. In case the latter part of his name wasn't enough of a hint, He's not.
 * Done by Alexandre Dumas in at least two of his novels.
 * In The Three Musketeers, there's an inversion of the good blonde and bad brunette, as the heroine, Constance, has dark hair, and Milady, the villain, is blonde and angelic looking.
 * In The Count of Monte Cristo, the villain Bendetto AKA Andrea has strawberry blond hair (making him a case of both Blond Guys Are Evil and Evil Redhead), and there's a comment in the text to the effect that he looked like an angel; unfortunately, that angel was Lucifer.
 * In the original Battle Royale, Femme Fatale Mitsuko was repeatedly described as an "angelic beauty". She convinced several of her classmates that she was in fact completely innocent and vulnerable. The movie upgraded her to Evil Is Sexy, while the manga turned her into an improbably buxom, demonic Broken Bird.

Live Action TV

 * One of the UnSubs in Criminal Minds was 13-year-old boy who used his innocent look to get closer to people and then kill them.
 * The original name given to Angelus from Angel was 'The One with the Angelic Face' which sounds nice, till you find out just how vicious Angelus was.
 * CSI "Las Vegas" had Justin Bieber star as a psychotic teenage murderer.
 * Fringe does this in

Music
"You look like an angel Walk like an angel Talk like an angel But I got wise ''You're the devil in disguise"
 * There's the lyrics to the Elvis Presley song "Devil in Disguise".

"''Beware of pretty faces that you find; A pretty face can hide an evil mind."
 * Johnny Rivers' "Secret Agent Man":

Video Games

 * Dahlia Hawthorne in Ace Attorney exploits this for all it's worth in every one of her appearances.

Real Life

 * Cracked.com presents 5 Adorable Animals That Are Turning To The Dark Side.
 * Dr. H. H. Holmes, sometimes known as America's first serial killer, was said to be strikingly handsome and trustworthy looking.
 * Ted Bundy was known for his handsome features.