Artie Ziff
Artie Ziff went to high school with Homer and Marge and has affections for Marge. He asked her to the prom but she left him after he tried to put the moves on her. Later, he comes back as a billionaire and tells the Simpsons that he is rich to try and win back Marge. Later, he gets in legal trouble and loses all his money when "the bubble bursts", and hides in The Simpson's attic.