Artie Ziff

"I thought we killed him!"

- Homer re-meeting Artie

"Agh-hem!"

- Artie's catch-phrase

"Fellow Classmates. Instead of voting for some athletic superhero or a pretty boy, you elected me, your intellectual superior, as your king. Good for you!"

- Artie's Prom King-acceptance speech

Artie Ziff was Marge Simpson's senior year prom date from high school. He has attempted to get Marge to dump Homer for him and he often attempts to kiss her.

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.

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 marble toothbrushes and 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).

When Artie 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. It appears he is alive, however, for in the Season 22 episode, "The Fool Monty," Artie's name is last on the list of people who want five minutes of revenge on Mr. Burns.

Treehouse of Horror
Artie reappeared in a segment of Treehouse of Horror XXIII, which is a spoof of the film Back to the Future. In it, he won Marge's heart during their date to the prom after Bart altered Homer's first meeting with Marge while time-travelling. When Bart returns to the present time, he finds that Artie is now his biological father and the family is extremely wealthy. Also, the children have inherited Artie's curly hairstyle. When the present Homer, who had spent the last decades stalking Marge, tries to intervene with the help of numerous Homers from several points in the past, Artie and Bart both fight them off with Brazilian Jiu-Jitsu. However, Marge, upon spotting them, becomes interested in all of the Homers and divorces Artie.

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