Plothole in Season 1, Episode 9
In Season 1, Episode 9 ("Wizards, Warriors, and a Word From Our Sponsor"), the trio + Mike the TV constantly struggle, but they eventually realize that the key to success in that game is that all four of them have to do an act together in order for it to work. Even in the final leg of the game, Bob is barricading the door while telling everyone else to get the chalice, only for Dot to realize that they all have to do it together.
When they reboot, Bob is astonished that he's not the warrior, saying that he's "always the warrior." This means that Bob has played this game many times before.
So... how the hell does Bob not already know full well what they need to do to win?