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Role in the series
Jake and his crew first venture to the bluff in the episode "A Feather in Hook's Hat", Jake and his crew decide to visit the Sing-Songbird to get a new feather for his captain's hat, after he ruined the first one she gave him in a game. Unbeknownst to the sea pups, Captain Hook also desires a new feather for himself, leading the greedy pirate captain to pursue the Sing-Songbird all over Neverland. When Jake and his crew catch up to the Sing-Songbird, she had finally returned to her nest atop a cliff in Buccaneer Bird Bluff. Captain Hook, still desperate for one of the Sing-Songbird's feather, disguises himself as a bird, but the young pirate team intervene and thwart Hook's scheme yet again. Eventually Jake asks the Sing-Songbird nicely for a feather for himself and one for Hook. At the end of the episode, Hook is overjoyed with the new feather replacing his original plume with the fresh feather. Unbeknownst to him, the new feather was the same color and size as the old one.
Buccaneer Bird Bluff returns in the episode "Mystery of the Missing Treasure!" In the episode, Jake and his crew discover that someone has stolen their Team Treasure Chest. Originally, the young pirates believed the thief was Captain Hook, but none of the various clues the pirates discovered on Pirate Island matched Hook and his crew. It wasn't until they discovered a brown feather and Skully suggested they journey to Buccaneer Bird Bluff to ask their feathered friends if they knew who the feather belongs to.The Sing-Songbird recognize the feather as one belonging to Fast Claw, the pet falcon of the sneaky, plundering pirate Beatrice Le Beak.