The Simpsons Episode 9.16 Dumbbell Indemnity

Moe falls in love with a beautiful woman named Renee. Renee, against all odds, actually requites his love. During their courtship, a new, tender side of Moe is revealed. All Moe wants to do is buy Renee gifts, and eventually he spends all of his money on her. Broke, he concocts a scheme that should net him some quick cash. Moe figures he can have his car stolen and then collect from his insurance company. The plan is brilliant, but Moe's first mistake is asking Homer to help him. Instead of following Moe's instructions exactly, Homer bungles his part of the plan and winds up in jail. Collecting the insurance money, Moe is torn between using it to take Renee on a romantic Hawaiian vacation or bailing his friend and erstwhile accomplice out of the pokey. Realizing it's time to fess up, Moe tells Renee of his financial problems and how he tried to solve them. She is accepting at first, but when Moe tells her he has another insurance scheme that will fix everything, she is disgusted and leaves him. Moe carries out this new plan, burning down his tavern and nearly killing himself and Homer in the process. Barney winds up saving his two buddies (after first saving a couple of beer kegs), and Homer allows Moe to use his house as a bar until his friend is back on his feet financially.