Artie Ziff

Artie Ziff was Marge Simpson's ex-boyfriend from 3rd-7th grade. He has attempted to get Marge to dump Homer for him and he often attempts to kiss her. He is he main antagonist and later an anti-hero of the Season 15 episode, "The Ziff Who Came To Dinner"; and returns as one of the two main antagonists in the Season 24 special, "Treehouse of Horror XXIII".

Artie met Marge in highschool while he was president of the debate club and invited her to prom after she refused Homer's offer of going to prom with him however he ruined the date after he tried to have sex with Marge who kept refusing which also resulted in her dress being torn.

Artie has since then became a wealthy billionaire after founding Ziffcorp but still tries to get Marge to divorce Homer for him so they could date and has made numerous attempts such as hiring numerous people to recreate prom night for him and Marge in order to redeem himself but forcefully kisses her during the dance and unknowingly causes Homer to witness his kiss and ultimately considers suicide as a result while working at an oil rig but Artie redeems himself by apologizing to them both and telling Homer that Marge will never him despite Artie's wealth.

However, Artie's worst act would be committed in The Ziff Who Came To Dinner where it's revealed he has been living in the Simpson's attic without their knowledge with Artie believing that Marge was his true love. The Simpsons reluctantly allow Artie to stay with them until he gets back on his feet however Artie's real reason for living with the Simpsons was because he is wanted by the Security & Exchange Commission after spending his Stockholders money for personal items but Artie betrayed Homer by proclaiming that Homer owned 98% of Ziffcorp after Homer had won the share through gambling effortlessly causing Homer to be sent to prison but Artie redeems himself by admitting that he was the original owner.