The core of the team actually WAS around for Jack and the other icons. Lora, I believe started choreographing Bill and Ted in the early 2000s. Mike was writing/show directing in the early 2000s. While their focus was on Bill and Ted, they did work closely with J. Michael Roddy—who ostensibly created the icons. Charles, I’m not sure the specifics of his trajectory, but he was there.
That’s what actually makes the lack of focus on the icons more telling. They were a part of their development. They saw the fandom build around them. And while the dynamics of HHN’s development has changed (pretty drastically), there still has not been a massive push for new icons to the scale if the aughts or a return to the classics.