Shantae: Half-Genie Hero

Story related, can't be missed.

This trophy will pop after you complete the DLC's first world by defeating the Tinkerslug/P.O.O.P.T.O.O.T. Defeat the Tinkerslug by attacking the bell, which causes an explosive barrel to be loaded at the top. Then use Bolo to climb up, launch the barrel at the slug then drop down to attack the slug. This should take about 4 barrels to beat with Bolo. You don't really need any other characters unless you need to heal, in which case switch to Rottytops.