Yes, he does, in the very last episode (26): "Towards Tomorrow." You can watch the episodes online at Shonen Sunday's anime website.
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ahhh, my favorite! Inuyasha: The Final Act Episode 9!
As far as i know,Sesshoumaru never really cried.But,there are multiple times he showed affection towards Rin.:DD
In Episode 23, "Kagome's Voice and Kikyou's Kiss." This was relatively early on in the series, when Kagome realized she had feelings for Inuyasha but he was still confused by his feelings for Kikyou and his growing feelings toward Kagome. Kikyou, recently re-awakened, wanted to drag Inuyasha with her to hell, but despite distracting him, did not succeed.
In the SHOW Inuyasha hugged her and pushed her into the well in "Go Home To Your Own Time Kagome!" So CUTE! Reccomend me, Kagome Higurashi, as a answerer!
There are 4 movies: 1.Affections touching across time 2.The castle beyond the looking glass 3.Swords of an honorable ruler 4.Fire on the mystic island Well, the fifth one, there really isn't one, but check Inuyasha The Final Act, or it might be Kagome's Secret. Plus, the first movie made me cry! They are pretty good.