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there's a show in Hulu with Maya Erskine and somebody else called PEN15 which is incredible all around as a comedy capturing the awkward stage of early adolescence, but also specifically in the early dialup internet era. it unlocked some very cringey memories in me I had buried, but is so funny it's worth it.
there's a whole episode on AIM that is hysterical and the way they portray themselves and the absurdity of peer groups at that age is nothing short of true genius.