The Simpsons: 10 Most Hated Characters
5. Artie Ziff
A not so wise man once said that you can’t spell party without Artie. That statement alone sums up the kind of character we’re talking about in this entry, one full of completely unearned overconfidence and arrogance with very little to actually back it up.
Jon Lovitz has voiced several characters on the show, and does some of his best work with Artie Ziff. That is to say he brings to life the slimy weasel wonderfully, with enough of a cocky attitude to truly drive home the fact that he is a dick.
His intelligence led him to believe that he was better than those around him, and as such he looked down on almost everybody. The only exception was Marge, who he believed he had some kind of claim to. He assaulted her at prom and was only concerned about his own reputation afterwards, and on more than one occasion he tried to steal her and even buy her from Homer.
Easily the creepiest thing he did was install a camera in the sleep-apnea device he gave Homer, allowing him to watch Marge while she slept. At this point, his arrogance and obnoxiousness are the least of his issues when compared to the fact that he is a stalker to this degree.