Pepper Ann
Date aired: 1997-2000
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Comedy about awkward teenager Pepper Ann, who only really has 2 friends, and manages to put other kids off by her slightly-nerdy behaviour, constant bad timing and insistence on trying to be cool. And to make matters worse, she's just started middle school, and has immediately caught the attention of the perfectionist principal, who's always on her case and waiting for her to screw up.