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Brittany Murphy on Boy Meets World (1995)
Still rocking her Clueless look as Topanga's BFF (the one who teams up with Shawn to finally get the pair together).
Mila Kunis on 7th Heaven (1996-1997)
Kunis had moved beyond Lisa Frank ads to play the middle school mean girl, an age-old type instantly recognizable to any woman who's had to deal with pre-teen politics. Though she starts out as Lucy's friend, she morphs into a boyfriend-stealer when she goes out with Jimmy Moon (who, for any fair-weather 7th Heaven fan who dropped out before the later seasons, grows up to get Lucy out of jury duty when she's assigned to his trial).
Jennifer Love Hewitt on Boy Meets World (1998)
The response to a stranger greeting you with a passionate kiss is rarely "you're friendly," but that's an issue for another slideshow. Hewitt is another victim of the creepy killer in BMW's slasher flick send-up episode.
Joseph Gordon-Levitt on That '70s Show (1998)
Gordon-Levitt is just so adorable here highlighting the ridiculousness of gay panic as one of Eric's few friends outside the haze of the basement circle.