Take a shot when Jon put a ridiculous costume item on someone else. Finish the bottle if the other person is still wearing it in the next video.
Take two if he puts hipster glasses on something or someone.
Take a shot every time Jon says, "Yeah coffee!" in the finale. Make sure your affairs are in order first.
Take a shot whenever Ness fights Pikachu in the SSB tournument
Take a shot whenever Chugga says "Press two" in the Mario Stadium board in Fortune Street.
Take a shot whenever someone rolls an "H" in any Fortune Street board. Take two if someone calls it an "H", unless it's the Slimenia board, in which case just finish the bottle and save yourself the trouble.
Take a shot in any Mario Party video where Bowser does the pee dance (and they comment on it). Take two if Bowser does his "sexy pose" in Mario Party 3.
Again in Mario Party 3, take a shot whenever Chugga says "(Character) takes it", when said character wins a minigame.
Take two shots whenever Chugga refers to himself as "the monkey."