That’s definitely old footage (you can tell by the hair, the voice, the “still making sense” vibe). I kinda missed his early internet phase, so for me his career looked like a speedrun: “Wow, this guy is saying sharp, logical stuff I can actually relate to” → straight into → “WTF is this clown show? He can’t tell his ass from his head… because, naturally: ‘Well, what do you mean by head? And what do you mean by ass? And what do you mean by mean, while we’re at it?’”