What Season: And Episode Does Naruto Fight Pain ((link))
While the arc builds up over several episodes prior, the actual hand-to-hand combat between Naruto and the Six Paths of Pain begins in Episode 163, titled "Explosion!"
However, if you are looking at the DVD releases or the overall series count, the Pain arc marks the end of the "Part I" era of Shippuden before the series transitions into the Five Kage Summit arc and eventually the Great Ninja War. what season and episode does naruto fight pain