In 1919, he made the first Itchy cartoon, entitled "Itchy the Lucky Mouse in Manhattan Madness". Roger Meyers, Sr. stole the idea from him and refused to pay him. Chester then became a bum for many years until he and Bart Simpson opened up a case against Itchy and Scratchy studios for 800 billion dollars. Chester and Bart won the case, making Chester incredibly wealthy. With his earnings, he bought a solid gold house and a rocket car. The payout to Chester from the studio lead to its downfall, so Bart and Lisa went to Chester to ask him to fund Itchy and Scratchy studios. When Lisa tried to convince him to do so with telling him he'll get royalties; Chester replied, "I don't need any more money. I'm not greedy, as long as I've got my health, my millions of dollars, my gold house, and my rocket car; I don't need anything else." Lisa then says, "Yes, but..." and is then interrupted by Chester saying, "Not interested." He then proceeds to go to sleep. He and Abe Simpson have a grudge against each other due to the fact that Chester was originally supposed to paint Abe's chicken coop in exchange for Corn Muffins back in 1947, but he rescinded the offer because his Corn Muffins tasted bad. He also has a grudge with Krusty who gave him a plate of blintzes to paint his fence which he did not do.
He makes a brief appearance at the Drunk Help Building where an unemployed Duffman is teaching in the episode Old Yeller-Belly. He's seen wearing his bum clothes, indicating that he probably lost his fortune.
During Trappuccino, Chester can be seen in the angry mob searching for the Simpsons. There he appears again with his old ragged clothes, furtherly proving that he returned to his homeless life.