There’s no denying that there have been some exceedingly strange moments over the course of Ash’s journeys with Pikachu and their friends. But Ash ending up with a Slowking’s Shellder on his head, resulting in a rap battle with Goh not once (“Slowking’s Crowning!”) but twice (“...
If they are the cause of trouble, he will stop them, and then try to understand them, with almost all such occasions being a case of the Pokémon, or their Trainers or friends, having a problem which can't be resolved normally. In those cases, he will selflessly volunteer to help them...