I know what you mean, like Twitch emoji Pepe's.

I think because of the time that has passed, there's a demographic that uses him without knowing and I think the stickers definitely are part of that. However I don't think that removes culpability, it's just how different generations interact with different words, or in this case meme.

And really I think what it comes down to is when meme becomes tied to identity. Sad Pepe is relatable, feel a connection to the character, see what other memes he can do, before you know it your discord emoji Pepe is a pipeline to normalizing political extremism.

Like how some subcultures create a pipeline to fascism, like cottagecore and tradlife. It's not necessarily that all Pepe, all tradlife, brings you into the path towards fascist ideology, but that many of those with fascist ideology are drawn towards Pepe and tradlife, which then make engaging with content surrounding those subjects suspicious.

Pepe in abundance is just something to be wary of. I don't think it's wrong to use him on discord or twitch chat, but I am more suspicious of people who identify with him heavily and I keep an eye out for the type of memes and rhetoric that they use. Chances are high that it's innocuous, but given his history I'd say it's better to be aware than to think nothing of it.

Last thing, for me it's mostly just odd because when I look up Pepe memes, so many of them are terrible. Not just bad memes I mean, like hateful and awful. Sad Pepe is pretty much the exception here, as in normal meme I still see him and it's used pretty in-line with what you would expect from normal memes.

Tl;Dr - sad Pepe or Pepe emojis on twitch/discord = probably okay. Identifying with Pepe or making Pepe memes = maybe I'll be keeping a closer eye on what exactly you're trying to say