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Not late 90's or early oughts, but I'd put a Vtuber or two on there (personally, I'd do either Fuwamoco or Mel [if Mel were still in Hololive]). Otherwise, because of the ThinkPad, and the OS you're using (which, from my experience, is a huge mistake if you're a beginner to Linux), I remember watching something from the 80's, that being Urusei Yatsura, so maybe Lum if you wanted to go that route. Otherwise, I'd say one of the characters from Rec!.
Lum would be a nice nod to the classics.
OP wanted 90's-early 00's, though I thought 80's could suffice of OP hadn't thought of it. I could try to find someone obscure too, but I think that's pointless for what OP requested.