My vote would be Grandpa Lou Pickles from Rugrats. He meant well with the kids and was malicious, but he had a way of flirting with some younger ladies that today would not be considered appropriate. I mean it was the 90s and was actually not malicious. But I'm just saying now it may be.
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Honestly, a lot of 90s cartoon characters would get side‑eyed today 😂 Grandpa Lou is a good pick.
For me, Pepé Le Pew from Looney Tunes is the big one. His whole “romantic” shtick is basically nonstop harassment of that poor cat. Back then it was played for laughs, but now it just feels super uncomfortable and stalker‑ish 💀📺