Artie Ziff

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

Personality
Artie is very confident yet nerdy, self-centered and pretentious, believing himself to be the best at everything - he said that it "would damage 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, and once commented that if people don't like him it's because they're Anti-Semitic. He holds a deep obsession over Marge, and has done so 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 Simpson 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, Artie was revealed to have become a software billionaire, becoming the fifth richest man in the country. His wealth came from a device that transformed 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's rejecting him on prom night.

Artie claimed that he would offer a small fortune for a weekend with his childhood love, Marge, in a parody of the movie . She accepted, as the money would come in handy, and he seemed harmless. He managed 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 slapped Artie and left. 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 found him, Artie finally admitted 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 revealed 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 into the Simpson home 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).

Prison
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—for the benefit of their health, whether they wanted it or not. Marge told the children to take a good look at Artie, as his actions dramatically lowered his chances of survival. The family's last view of Artie was of him continuing to squirt other prisoners' cigarettes while an ever-growing angry mob advanced on him.

Release and later history
Artie survived the prison yard encounter and was eventually released from prison. He later revealed that he had negotiated an early release by ratting out other CEOs for their crimes, and regained his fortune when they paid him off to keep him quiet.

His name was seen on a list of Springfieldians taking revenge on Mr. Burns.

Later, Artie invited Homer and Marge to attend his wedding. When they arrived, Homer was asked to walk the bride down the aisle as she didn't have anyone to do so. When the bride took off her veil, she was revealed to look exactly like Marge. After the wedding, Homer and Marge confronted Artie and his wife only to find that the Marge Artie married was a robot, and that Artie had made several other Marge robots. Artie wanted to make Marge realize how perfect she would be with Artie by planning a fake wedding to a copy of Marge, but it failed. Marge then told Artie that he could use his brain to help people rather than try and win her heart.

Non-canon
When Marge decided to break up with Homer, Lisa found a talking picture of Artie telling Marge that it was good that she finally left Homer and that he had finally learned how to unhook a bra with one hand.

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.