Artie Ziff

Artie Ziff was Marge Simpson's high school prom date.

Personality
Ziff is very confident yet nerdy, self-centered and pretentious, believing himself to be the best at everything - he said that it "would damage reputation of the town" if Marge told people about his "busy hands", and once imagined a can-can chorus and audience made up entirely of himself. He is Jewish, once commenting that if people don't like him it's because they're Anti-Semetic. He holds a deep obsession over Marge, and has done since high school: His appearances mainly revolve around his plans to seduce her away from Homer, with the exception of his final encounter with the Simpsons family.

High School
Artie was a student at Springfield High School. He was a member of the school Debate Team (where Homer mooned him for rebuttal), and at the end of the year took Marge to the prom. He ruined a wonderful evening with his "busy hands" in the back of his car, his urges resulting in the shoulder strap of Marge's dress being torn, followed by a slap to the face and a swift end to their date. He drove Marge home.

Wealth
Many years later, he was revealed to have become a software billionaire, becoming the fifth richest man in the country. His wealth came from a device that transformed modem noise into easy listening music. Despite his riches, Artie's life was not complete: He lived alone, and the collection of Marge-resembling art around his mansion showed that he never got over Marge rejecting him. Artie claimed that he would offer a small fortune for a weekend with his childhood love, Marge, in a parody of the movie Indecent Proposal; she accepted, as the money would come in handy, and he seemed harmless. He manages to trick Marge into kissing him at a full recreation of their high school prom (including most of the original guests), which Homer witnessed. She slaps Artie and leaves. After a fruitless search for Homer, who left believing that they were having an affair, she enlisted Artie's help, using his helicopter to find Homer and bring him home. When they find him, Artie finally admits defeat to Homer, saying that winning Marge's love was something that he could never accomplish, even with his billions.

Ziffcorp
Some time later, the Simpsons discovered that Artie was living in their attic. He reveals that he ran his company, Ziffcorp, into the ground spending investors’ money on such extravagant items such as solid gold underpants. He was left penniless when the "dot-com bubble" burst, and secretly moved there to avoid capture. Homer won 98% of the company from Ziff in a game of poker; seconds later, SEC agents came to take Ziff, but they took Homer into custody instead (as he had just become the majority shareholder).

Possible Death
When Artie Ziff finally turned himself in, one of his first acts upon arriving in prison was to begin extinguishing other prisoners' cigarettes with a squirt bottle (allegedly to save their lungs). Marge told the children to take their last look at Artie, as his actions dramatically lowered his chances of survival. Artie was last seen continuing to squirt other prisoners' cigarettes while an ever-growing angry mob advanced on him. What happened to Artie after that (or even whether he survived the encounter) isn't known. Although in the season 22 episode, "The Fool Monty", Artie's name is last on the list of people who want 5 minutes of revenge on Mr Burns. .

Behind the laughter
Artie Ziff was voiced by Jon Lovitz on his first appearance in the Season 2 episode, "The Way We Was" and occasionally by Dan Castellaneta in the later episodes.