They don't have to be gen 1-3 pokemon. In fact, I'd prefer if they were newer gen pokemon capable of giving this feel. First Mon that comes to mind is Mimikyu. Definitely gives off like Gir from Invader Zim, and the sort of edgy depressive vibe that I want to feel. Please post images that capture this sort of... Feeling.

>>57945718 (OP)
Lots of sinnohmons like Weavile and Skunktank

>>57945732
Its got a close vibe for sure. I like the idea of a mon like Skuntank. Like, its gross, kinda ugly, and nasty, but thats kinda what makes it perfect for a sort of rebellious attitude. To reclaim a cringe phrase, "fuck your beauty standards". Because not everything needs to be pretty all the time.

Darkrai is peak edgy depressive oneiro vibes.

>>57945718 (OP)
gonna go with a very oddball choice with Mabosstiff. it's a big fluffy dark type dog with a constant sad look on it's face, but can get fierce looking when "on guard". I feel certain trainers of that vibe would 100% find a sort of mutual love for it.

>>57945718 (OP)
Absol, Grachomp Mightyena, Darkrai, Zoroark, Weavile, Banette, Mawile, Houndoom, Skuntank, Zangoose, Seviper. Lots of Hoenn mons funny enough

>>57945718 (OP)
absol
>>57945732
lol my second thought was toxicroak

>>57945718 (OP)
maybe these arent angsty so much as grunge, but i always felt like barbaracle and the golisopod line are really grunge, dingy sort of awkward or sour disposition.

i can imagine being a social outcast in mid 90s portland and finding these two creeps nobody wants or cares for while wondering around some overcast beach

Both were even designed by Sugimori even.