The Simpsons: 10 Best Villains Ever
3. Artie Ziff
Right from his debut, Artie Ziff is an absolute lech and he only gets worse with every appearance. It’s no surprise really; Jon Lovitz has made a career from being an onscreen creep.
First introduced as Marge’s prom date with busy hands, he’s since reappeared living in The Simpsons’ attic sucking on ceiling moisture, framing Homer for his financial crimes, and offering an indecent proposal for a weekend with Marge to restage the prom.
It’s this unyielding obsession with Marge, founded on the desire to sleep with her rather than any notion of love, which makes him so villainous despite being a dweeby pushover.
The various paintings and statues of Marge scattered around his mansion; this is the type of thing serial killers do. Admittedly, very well off serial killers given the mansion, but still. It gets brushed over because it’s a two-second gag supposed to show that Artie never moved on from their failed prom date, but it’s creepy beyond belief.
That’s before you notice that several pieces of art depict a modern Marge with the red pearls, green dress and much taller beehive. So he may have been stalking her all these years, too.