Artie Ziff, voiced by Jon Lovitz, is probably best known as Marge Simpson's former high school prom date in The Simpsons universe. As seen in the episode "The Way We Was", Artie was a forensics club champion and generally respected junior member of the community. After Marge canceled her date with Homer Simpson (when she learned he had been lying to her about needing some tutoring), Artie asked her out (in a forensics format and using quotes from Time Magazine to help convince her). She accepted.

On the night of the prom Homer arrived to pick up Marge at her home. In a classic dense Homer moment, he was unaware that when Marge told him that she never wanted to see him again, that also meant that the date was off. After being humiliated in front of the Bouvier family, Homer left to go to the prom by himself just as Artie arrived, who quickly earned the respect of the family.

At the prom Artie and Marge danced the night away, had their picture taken, and were even pronounced Prom King and Queen. It was a magical evening, although later, at Inspriation Point (a local cliff perfect for making out), Artie's busy hands went too far and, during an unwanted attempted seduction, tore away a strap of Marge's dress. Angry, Marge proclaimed the date over and ordered Artie to drive her home. After this incident, which was told in a flashback in the second season of the show, Artie was not seen again for many years. There was a single, brief encounter at a high school reunion (not voiced by Lovitz) where he was heard to say "Have you heard? I'm stinking rich!", but the next major encounter with him would not come until 2001 in the episode "Half Decent Proposal".

Homer and Marge eventually married, of course, and after many years together Homer's snoring problem was becoming too much for Marge to bear. An expensive surgery could correct the problem, but the Simpsons could not afford it. One night Marge decided she needed at least one night of rest, so she went to stay overnight with her sisters, Patty and Selma. It was during this evening that the three sisters had a little too much to drink and, in their haze, e-mailed Artie to say hello and how much Marge wanted him (a bit inserted by her sisters). Before Marge could object, the message was flying through cyberspace where it eventually reached Artie himself. "Hmm, Marge Simpson," he said at the time, "What a coincidence. I was just thinking about her... for the past twenty-five years!" The camera pulled back dramatically, revealing that Artie's office was plastered with various photos and paintings of Marge herself.

Much had changed for Artie since high school. His company's main product was a device that turns modem static into pleasant music (with or without lyrics). As a result of this invention he was quite wealthy and, having come back to Springfield in his private helicopter, offered Homer the money he needed for the snoring surgery in exchange for one night with Marge. As long as there would be no sex in this arrangement, the family decided to accept the offer.

Whisked away to Artie's estate, Marge was shocked; Artie had recreated the entire prom! The two danced just like old times, but when Artie asked for an innocent kiss, he plastered a deep liplock on her. Unfortunately, Homer had been spying on them from elsewhere in the room, developed the totally wrong idea about what was going on, and decided to leave town with his friend Lenny to become oil riggers.

What Homer didn't see what Marge slapping Artie away, just like so many years before, and proclaiming the evening over. She returned home, found that Homer had left, and chased after him. In the end everything returned to normal, and although the family didn't get the money they needed for Homer's surgery, they were given Artie's newest product: a mask which turns snoring noise into pleasant music (in this case, Sweet Dreams by the Eurythmics). More sinister, however, was that a secret speaker and camera were inserted in the device, allowing Artie to watch Marge sleep and allowing him to chant suggestions such as "He's a loser, Marge. Dump him." while she slept. Presumably someone in the household found out about this creepy feature, as Homer was never seen on the show wearing it again.

In 2004 Artie came crawling back to the Simpsons in need of help. After the dotcom bubble burst he lost his business and his fortune. Left with nothing, he took up residence in the Simpsons attic (uninvited, of course). Once his presence was revealed the family invited him to stay, and it wasn't long before he had framed Homer for financial fraud. Eventually he did confess and is currently serving a sentence in prison.

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