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Jeremy "Jay G" Gilroy, is a rapper and owner of the Golden Goose brand and a former member of the rap group The Five Boyfriends.

When Mr. Burns and Homer try to crash a party, they discover that the host, Jay G, likes Mr. Burns as he is his role model after reading his book, The Rungs of Ruthlessness, which he found on a bus that he hijacked once, and thanks Burns for making him become who he is. After this, Jay G and Mr. Burns bond and become friends.

Jay G brings Homer and Burns on his private plane and gives Burns a special credit card for him to use. He invites Burns, with Homer tagging along, to buy a lot of stuff for really high prices, and slowly emptied out his bank account.

Burns soon finds out his trouble are worse, as his card is declined, as he is broke. Jay G's repo men come to his mansion to retrieve all his high expensive belongings. Homer then shows Burns a music video Jay G made, called "Monty Burnt", and he is reduced to crying after finding it out, as he had hit rock bottom...