Artie Ziff

Artie Ziff, voiced by Jon Lovitz and occasionally by Dan Castellaneta, was first seen as Marge Simpson’s high school prom date with “busy hands” (“The Way We Was”).

Personality
In “Half-Decent Proposal” he was revealed to have become a nerdy, self-centered, and pretentious software billionaire, becoming the fifth richest man in the country.

Wealth
His wealth came from a device that transforms modem noise into easy listening music. He claims that he would offer a small fortune for a weekend with his childhood love, Marge, in a parody of the movie Indecent Proposal.

Ziffcorp
When Ziff returns yet again, in The Ziff Who Came to Dinner, this time living in the Simpsons’ attic, he reveals that he ran his company, Ziffcorp (a parody of Enron), into the ground spending investors’ money on such extravagant items 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 instead took Homer into custody.

Possible Death
When Ziff eventually turned himself in, one of his first acts upon arriving in prison was to begin extinguishing other prisoners’ cigarettes with a squirt bottle. Marge told the children to say goodbye to Artie, as they may never see Ziff alive again. He has not appeared since.