I meant "punk rock" in a "refusal of rules" or (in combination with "hackerman") "creative use of tools/methods". To elaborate further, when you read him you often feel like he claims his Simulacra Theory is universal, and he further makes quite bold claims like the Gulf war did not happen, reality is not real and is produced by culture/media. Those are not scientifically rigorous claims. But he makes those (at first reading outlandish) claims, not to craft theory, but to invite exchange with his theories, to challenge reality, not to make scientific theories.

A little disclaimer he was a very serious academic. I just think in his later works he kind of "defected" knowingly from the scientific method.

About your second part: > If your philosophy isn't targeting your average person with their average existential crisis, you have failed your mission.

Debord has a long paragraph about this in "society of spectacle", that the way forward is to make the worker a dialectician.

You claiming that "Philosophers have completely failed their mission since the greeks" is understandable, but I think empirically false. Quite often, ideas shape in culture, get picked up in philosophy, get reshaped, refined and influence culture which is targeting the average person. A good example to show that is Existentialism and Nihilism. Nietzsche, Kierkegaard, Camus and Sartre worked out the kinks, then it returned back in modern culture e.g. as Rick and Morty which is translation of academic ideas to the average person. I do agree though that the transmission rate of this process could be better. This very discussion is a hint on that, most non-academia people know Baudrillard through the Matrix-Franchise, which, ironically, Baudrillard hated and in my opinion did not translate his ideas at all.