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Bobbery is an old Bob-omb sailor who lives in Rogueport. Mario looks for him as a navigator to Keelhaul Key, which is surrounded by treacherous reefs. Bobbery is adamantly against it at first for an unexplained reason. A nearby bar tender explained about when Bobbery was younger, he had a beautiful wife named Scarlette. One time when Bobbery was at sea, Scarlette went down with a mysterious illness and eventually died, convincing Bobbery never to sail the seas again.  If Mario gives him a letter written to him by his wife in her final hours, he agrees to come along. After the shipwreck, Bobbery is separated from the crew and looks like he will die, giving one last request: to drink a bottle of Chuckola Cola.  After going through hurdles to get the only bottle of Chuckola Cola from Flavio, Mario and co. bring it back to Bobbery, and he seems to finally die, but in reality, he falls asleep.  However, he manages to pull through, because as it turns out, he fell asleep instead of dying.  He joins Mario on his journey after he is woken up.  In the field, Bobbery can walk forward a few steps and explode, and due to the way he is deployed, he can be thrown up ledges that not even Mario himself can reach.  This is a good way to start fights with enemies as well as blow up certain wall segments. In battle, Bobbery is arguably the most powerful partner in the game (rivaling Vivian), with strong explosive attacks including the most powerful attack in the game, Bob-ombast.

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