The 10-year-old's exes haunt him in the season 24 episode "Moonshine River"
Bart Simpson, ladies man? You might not think so, but he’ll go “High Fidelity” when he revisits a bevy of exes — played by Zooey Deschanel, Natalie Portman, Anne Hathaway, Sarah Michelle Gellar and Sarah Silverman — next season.
Fox confirms to TheWrap that the actresses will reprise their guest roles as Bart’s former love interests, in an episode called “Moonshine River.” It will find the 10-year-old wondering if he let the love of his life slip away. EW.com first reported the guest appearances.
The exes — Deschanel as Mary (pictured at bottom, right), Portman as season 18′s Darcy, Hathaway as season 20′s Jenny, Gellar as season 15′s Gina and Silverman as season 21′s Nikki — make quick appearances that spark Bart to wonder if maybe the old “it’s not you, it’s me” breakup line is actually true, and whether he is actually to blame for why all his romances went kaput.
“It was a way to acknowledge that for a 10-year-old boy, Bart has gotten a lot of action,” “Simpsons” consulting producer Tim Long, who wrote the episode, told EW.com. “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.”
Ultimately, Bart heads off on a road trip to New York to find Mary — daughter of hillbilly Cleetus and the girl Bart almost married in season 19 — which will include Mary/Deschanel singing an original song to him.
“Any resemblance between this episode and ‘Breakfast at Tiffany’s’ is completely coincidental, Long told EW.
Meanwhile, other guest stars already lined up for season 24 include Steve Carell (who’ll play Fat Tony’s accountant), “Portlandia” stars Fred Armisen and Carrie Brownstein, Jennifer Tilly, Joe Mantegna and Anika Noni Rose, who’ll play a former girlfriend of Grandpa Simpson.
“Simpsons” producer Al Jean also spilled in an interview with GiveMeMyRemoteTV.com that the series’ next Halloween episode, “Treehouse of Horror XXIII,” will include a “Back to the Future”-inspired segment about Marge and Homer’s marriage, featuring the return of Artie Ziff (Jon Lovitz).