THE GUEST: Anne Hathaway
THE CHARACTERS: Jenny (from ''The Good, the Sad and the Drugly,'' 2009) and Princess Penelope ([pictured], from ''Once Upon a Time in Springfield,'' 2010)
In less than a year, the Oscar-nominated actress managed to both tame the prankish Bart Simpson and woo the greasepaint-encrusted heart of his idol, Krusty the Clown. In the latter episode, the show's 450th, she adopts an endearing Lawng Island accent and employs her classically-trained singing chops to play the prickly Punchinello's studio-enforced co-host and eventual fiancée. No word on who'd get Mr. Teeny in a divorce. Keith Staskiewicz
Image Credit: Simpsons: Fox; Hathaway: PR Photos
As the animated series hits its 500th episode, we look back at Springfield's most memorable visitors' voices, from Lurlene Lumpkin (Beverly D'Angelo) to Jessica Lovejoy (Meryl Streep) to Sara Sloane (Marisa Tomei)