The Simpsons Season 33 Episode 15 - Bart the Cool Kid Episode Title:Bart the Cool Kid.Episode Description:Homer promises to buy Bart a pair of limited edition sneakers only to buy bootlegs instead. When Bart tries to return them, he is humiliated publicly and declares that Homer is the least cool person ever. When young shoe creator Orion Hughes feels sorry for Bart and donates his branded skate wear and merch, Bart learns that the famous kid influencer cannot actually skate himself. Meanwhile, a dejected Homer uses Orion's gifted clothing to influence other middle-aged men to dress in hip threads to prove they can be cool.