The Episode: "New Kid on the Block" (Season 4, Episode 8)
The Voice Actor: Sara Gilbert
These days The Simpsons is known less for its candid exploration of romance and more for its zany, Family Guy-esque antics, but there was once a time when an episode could paint that thing we call love with real depth and accuracy.
Case in point: Laura Powers. Bart fell for this cool, Army jacket-wearing character in season four, and she served as a kind of epitome of "the older girl" type that so many pre-teen boys will have encountered at one time in their lives.
As Bart's babysitter, Laura, brilliantly voiced by Sara Gilbert, allowed audiences a window into a more emotional, vulnerable Bart, who - up until then - was mostly associated with school yard pranks and crass toilet humour.
But Laura herself is more than a caricature: there's a warmth to this teenager, despite of the fact she's way more interested in idiot Jimbo Jones than Bart. We believe she has the power to break his heart, and in the process of her doing exactly that, Laura became an unforgettable one-time Simpsons legend.