Sarah Michelle Gellar

When Bart’s love life heats up again on The Simpsons, it will involve an old flame or two. Actually, make that five. Not only will Zooey Deschanel guest-star on the animated comedy by reprising her role as Mary Spuckler — that adorable hillbilly daughter of Cleetus whom Bart nearly married in season 19 — four other former girlfriends, voiced by Natalie Portman, Anne Hathaway, Sarah Michelle Gellar, and Sarah Silverman, make cameos in the same episode, EW has learned.

Why are so many of Bart’s past loves returning at once? “It was a way to acknowledge that for a 10-year-old boy, Bart has gotten a lot of action,” explains Simpsons consulting producer Tim Long, who wrote the episode. “We thought it might be fun to borrow/pay homage to/steal an idea from High Fidelity and have him go on a romantic pilgrimage and visit the girls that he dated and try to figure out how the hell he screwed things up with each of them… I don’t want to give away too much, but he realizes that maybe there’s something wrong with him after all.”

Early in the episode, ex-girlfriends from the last decade such as Gina (Gellar, season 15), Darcy (Portman, season 18), Jenny (Hathaway, season 20), and Nikki (Silverman, season 21) pop up briefly. But when Bart learns that Mary has relocated to New York, he decides that she’s the one that got away and embarks on a mission to track her down. (As Mary, New Girl’s Deschanel winds up singing an original country ode to Bart.) “Any resemblance between this episode and Breakfast at Tiffany’s is completely coincidental,” quips Long.

“Moonshine River” is scheduled to air on Fox in the fall as part of the show’s 24th season, which will feature vocal contributions from Steve Carell, Jennifer Tilly, Fred Armisen, and Carrie Brownstein.