It wasn't Shakespeare or Harry Potter, but it was British:
Tony Noland was the first to enter, saying:
The British legal system, in Bleak House. Many lives destroyed by Jarndyce and Jarndyce.
Katherine Hajer was second, also pegging Dickens’s Bleak House:
Any antagonist who does evil in the name of kindness or righteousness. Let's go with Tulkinghorn, then. I don't know about "most", but he's a great example.
Then Larry Kollar asked:
How about Satan in The Book of Job? Ruined his life & health on a bet.
Dave Cornford said:
Nils Bjurman from Larssen's Millennium trilogy. Few to choose from in those books.
Catherine Russell said:
Okay, well in print (but MEANT to be performed) Iago from Othello is the most despicable imo because he ruins lives for no other reason than sheer spite and jealousy.
Helen Howell said:
For me it's Voldemort from Harry Potter, because he's power mad and will try to destroy anyone who stands in his way.
Joshuo Londero said:
In The Beastly Beatitudes of Balthazar B the main character meets a little boy at boarding school of the same name. He goes by the nick-name Beefy. They become life-long friends, but Beefy has a way of turning everything to shit. He is one of the most vile, despicable and endearing characters I have ever met.
Beverly Fox said:
Baby Kochamma from The God of Small Things because she destroys lives using the most age-old weapons available: religion and manipulation.
Cynthia Schuerr said:
Jane Hudson in Whatever Happened to Baby Jane? She was frightful. It's very old and not many may remember the horrible things she did to her sister. But she was truly despicable. She kept her sister locked up and tormented her physically and emotionally.
Chuck Allen said:
I vote Mrs. Coulter from Pullman's His Dark Materials trilogy because crimes against children seem especially evil to me.
Eric Krause said:
I'd say Pennywise the Clown from Stephen King's It has to be up there. Just the way he gets Georgie at the very beginning would put him on the list, and he's just getting started there.
Jemma Mayer said:
For despicability, I nominate the Patriarch Rostov from Jacqueline Carey's book Naamah's Curse. Over the months of her captivity, he forces the main character to tell him about sleeping with the multiple people she's fallen in love with, one of whom is now dead, and tells her it's a sin, sullying her memories of her loved ones and her opinion of herself. He's sadistic too, of course, but I hate that he tries to turn her own thoughts and feelings against her.
And just before midnight on the deadline, Randall Nichols wrote in:
Darcy Parker from Strangers in Paradise - alive, she was little more than your average, mustache twisting villainess, sporting all the cliches of manhating, weaponized sex, incest, pimping, and organized crime. But the way the specter of her and her actions hovers over Katchoo's life after she's already died, sucking in David, Casey, and even the the seemingly unshakable amazon Tambi [the woman who killed her] is her true evil - by having a hand in bringing almost of all of Katchoo's loved ones into her life, she poisons almost ever relationship a damaged woman has.
If you have your own opinion, feel free to drop it in a tweet or in the Comments below and I'll add you in. Now that we've come to the end, you may ask: "What's our host's opinion?"
Well, I do have one, and I'm unsurprised no one picked it. I kept it down to an honest Tweet-length.
The kid from Shel Silverstein’s The Giving Tree. After everything else, he even takes the tree’s pathos.