https://en.m.wikipedia.org/wiki/Freedom_of_Speech_(painting)

But most often used on Hexbear as either an equivalent to OR to make fun of someone for speaking their very dumb truth OR thanks to the layers of irony that everything on Hexbear has to actually express admiration for the view a person has stated.

or just that it'd be funny to imagine the guy in the picture saying that

It's all about context. In this case, if someone stole the floor at a town hall to announce that "whoever first created autoplaying videos should be impaled" most people would definitely look at them confused and a bit appalled but we'd probably applaud it.

Oh and for broader internet meme lore: https://knowyourmeme.com/memes/freedom-of-speech-norman-rockwell-painting

I have no idea, it's of some libertarian guy talking at a hearing about uh, school funding? Idk how to get emote lore.

I think it's a Norman Rockwell painting called "Freedom of Speech."

No way! How did I not know that, TIL