i think for me, the funniest moments would be...the whole filler episode of when the imposter rock lee n might gai try to act as the real ones, and everyone knows they are fake except for naruto.LMAO
as for the manga...its between when naruto says that haku is hotter than sakura without knowing haku was a boy..lol and when the crow of itachis genjutsu gets stuffed into narutos mouth.lol