Simpsons Season 4, Episode 12: Marge vs. the Monorail

After Mr. Burns is caught storing his excess nuclear waste inside Springfield Park's trees, he is ordered to pay the town $3 million. The town is originally set to agree to fix Main Street, but the charismatic Lyle Lanley interrupts and convinces the town to use the money to buy one of his monorails. The town embraces the suggestion and Homer is hired as the conductor, but the only person remaining not so pleased about the whole situation is Marge.