The Simpsons' enduring popularity and lengthy run mean that the show has featured some of the world's most famous stars. While many appear as comically over-the-top versions of themselves, some get to join the grander tapestry of Springfield as unique figures in the series -- several of them playing Bart Simpson's various love interests.

Considering the episodic nature of the series, it makes sense that Bart would end up with plenty of one-episode girlfriends, crushes and infatuations. But that archetype has been used as a means to bring some of Hollywood's most impressive actresses to Springfield, making Bart's romantic history akin to a Tinseltown hall of fame.

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Sherri and Terri are Bart's most consistent reoccurring love interests. Originally played by Russi Taylor, then recast with Grey DeLisle following Taylor's death in 2019, the twins frequently appear as supporting characters at Springfield Elementary and Season 27's "Barthood" revealed a teenaged Bart would genuinely enter a romance with Terri. Taylor and DeLisle are both superstars in the voice acting industry; the former voiced Minnie Mouse for 33 years and the latter has appeared in several animated shows like Star Trek: Prodigy (in the episode "First Con-tact") and as Wonder Woman in an installment of Teen Titans Go!, which was recently renewed for Season 8.

But other household names have appeared as one-episode love interests for Bart. Season 4's Laura Powers -- voiced by Roseanne and The Big Bang Theory star Sara Gilbert -- was an early example of this kind of role, but her position as a teenager Bart developed a crush on left her with a greater disconnect to the character. Bart would actually gain a major love interest in Season 6's "Bart's Girlfriend" in the form of Jessica Lovejoy. She was voiced by Meryl Streep, one of Hollywood's most beloved actresses. Reese Witherspoon would follow Streep in Season 13's "The Bart Wants What It Wants" playing Greta, the daughter of actor Rainier Wolfcastle who ends up in a love triangle with Bart and Milhouse.

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The Simpsons Mary and Bart

Season 18's "Little Big Girl" introduced Natalie Portman as Darcy, a sweet-natured teen who forms a romance with Bart initially unaware of his age. Season 20's "The Good, the Sad and the Drugly" centered around Anne Hathaway as Jenny ahead of a different (and award-winning) performance as Princess Penelope. Sarah Silverman's Nikki debuted in Season 21's "Stealing First Base," while Season 22's "Flaming Moe" featured Alyson Hannigan as Melody and Carice Van Houten -- best known as Melisandre from Game of Thrones -- appeared as Milhouse's Danish cousin Annika, who caught Bart's eye in Season 26's "Let's Go Fly a Coot."

Some of Bart's love interests have stood out more than others, though. Sarah Michelle Geller's Gina from Season 15's "The Wandering Juvie" was an interesting foil for Bart: a hard-edged bruiser with a surprisingly soft spot for the troublemaker that could have been further explored. Amy Poehler's Jenda was teased as Bart's eventual wife in Season 16's "Future-Drama" and Season 25's "Days of Future Future," becoming the mother of his children before divorcing him. And Bart's most interesting love interest was Zooey Deschanel's Mary Spuckler, the musically-gifted daughter of Cletus. Simpsons viewers likely recognized some if not all of these names at the time, but it's neat to realize that many of Hollywood's biggest actresses are connected through a single goofy TV show.

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