After the events that transpired at the Weather Station, Ash and co. finally arrive at Fortree City. Ash couldn't wait to challenge the Gym Leader, unfortunately the Gym Leader is helping with the Feather Carnival. Later they meet the Gym Leader, Winona, who scheduled in Ash's request for a Gym Battle, but in the meantime they should have some fun. Meanwhile Team Rocket has plans of their own. What sinister plot are they up to this time, and why does the carnival bring back such bad memories for James?
James' Chimecho was the second Pokémon to be caught by friendship. The first being Cacnea and the third being his new Yamask.
The title could be referencing the 1981 song "Who's Crying Now" by Journey. It can also reference the phrase "Who's Laughing Now?".