The Simpsons: All Of Bart's Love Interests, Ranked Worst To Best
2. Jessica Lovejoy
Jessica Lovejoy is arguably the most well known of Bart’s love interests, with Meryl Streep’s role as the badly behaved minister’s daughter a classic character from the sixth season. Since he only had a crush on Laura Powers but never dated her, Jessica also marks his first real girlfriend.
Its place firmly in the middle of the Golden Era aids her memorability, as does the fantastic storytelling that goes along with those early seasons. The scene where she skateboards down the hill with Bart, only for various spillages to sabotage him along the way, is one of the best examples at the simple humour that made the show so endearing.
Having Bart act nicely to get her attention definitely worked better here than when it was rerun with Jenny, especially with Jessica’s true nature hidden underneath. Having her only want him to be a bad boy was a great twist on Bart’s pseudo-redemption arc too.
She just misses on the top spot because while she’s a fantastic guest character, she doesn’t fully lean into being a love interest. The winning girl has a more lasting effect on Bart, even if Lovejoy is more memorable in the overall canon.