1. Hanzo's Tragic End: Hanzo, a powerful ninja in Akatsuki, met a painful demise. Defeated by Maitake, he chose to sacrifice himself by being devoured by sharks to protect the organization's secrets. His death was excruciating, and he wished for a quicker end. 

2. Orochimaru's Experiments: Orochimaru, a notorious villain, conducts painful experiments on female subjects in his lab. Injecting them with deadly substances, the agony is unbearable, yet Orochimaru always manages to save them. These subjects would prefer a swift death. 

3. Karin's Unrequited Love: Karin, a popular character, longs for Sasuke's affection. She enjoys being bitten by him, despite the pain, considering him more important than her own life. Bite marks cover her body, evoking pity. 

4. Danzo's Tragic Fate: Danzo aspired to be the Hokage but his extreme methods backfired. A clash with Sasuke resulted in his defeat and the loss of his right arm. His attempt to seal Sasuke failed, leading to his death. He faded away in darkness.

5. Uchiha Shin's Torturous Power: Uchiha Shin, a follower of Itachi, underwent Sharingan transplants, gaining immense power. However, each battle was excruciatingly painful for him.