Naruto vs Bleach

Connection:

Both are edgy deuteragonists of their respective series which are the mostly highly regarded Shonen Jump animes and are rivals to the main protagonists (Naruto Uzumaki and Ichigo Kurosaki respectively)

Both were antagonistic at first after a betrayal (Sasuke abandon Konoha to join Orochimaru and Uryu betrays Ichigo), but eventually turned to the side of good to fight the bigger threat (Madara Uchiha/Kaguya Otsutsuki and Yhwach respectively)

Both are considered to be the last of their kind (Sasuke is the sole survivor of the Uchiha clan massacre and Uryu is the last Quincy after the Thousan-Year Blood War against Yhwach)

Both are also voiced by Noriaki Sugiyama in the Japanese Dub