I watched the portion where Henry was telling the story of doing psychedelics with Mike Tyson. (They did that poisonous toad licking thing).
He and Joe had smoked some weed, so I don't know if this is more about Henry being high or just being a dork, but he came off so desperate to name drop during that segment. Joe was focused on the psychedelics but Henry was just SO thirsty to tell his story about hanging out with Mike. It was the level of cringe I would have anticipated, but this time it was clear it was just him, not part of any schtick.