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I watched the two Cilan specials before Journeys. I'll watch Iris' special further into Journeys, before she shows back up.
Of the two new traveling companions in BW, I think Cilan had the bigger shoes to fill. People loved Dawn I'm sure, but at that point, they must have accepted that each series would have a new girl. Brock on the other hand had been there since the beginning, and even though he had a diminished presence in DP, he still played the role of the voice of reason, the battle explainer, the team mom, and the episodic butt monkey. Having Cilan start out as an ersatz- Brock also didn't help. Iris could be an ersatz-Misty without much trouble, because that was a dynamic that Ash hadn't had in two series. But doing what Brock did but differently just made Cilan come off as a non-union Brock-equivalent. I just wish he had as compelling a reason to join Ash as Brock did. "I lost my childhood to my deadbeat parents leaving me to raise my siblings" is quite a step away from "I want to be a better sommelier, and Ash tastes interesting."
Cilan's at his most endearing when he's being autistic and embarrassing the shit out of Iris, whether its about Pokemon battling, trains, movies, detectives or fishing. So his special with Clemont ended up showing off his good traits much more strongly than his special with Brock. Watching him hit all of his favorite nerd moments with Clemont and Bonnie reacting struck a much better tone than being serious in stopping a Gyarados from rampaging. I'm glad he got to go out on a much higher note (until MPM) than the departure episode of BW. The dude got majorly fucked over in Decolore.
