The Sing-Songbird first appeared in the episode "A Feather in Hook's Hat". Jake and his crew decided 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 wanted to replace his feather as well with the aide of his scurvy crew he found the Sing-Songbird in the Never Land Jungle. Hook demeaned the bird to give him one of her feathers but she refuses causing the captain to chase the bird all across Neverland. Tiki Forest was the first location The Sing-Songbird tried to hide from Captain Hook. Hook tries to force the Tiki Trees into revealing the where about of the Sing-Songbird but they refuse. Jake, Izzy, Cubby, and Skully trick Hook, and his crew disguise as Tiki Trees pointing them in the wrong direction.
Jake and his crew soon find the Sing-Songbird near the beach between Coral Cove singing with Sandy the Starfish briefly before Hook and his men return still determined to have the bird feathers, Jake and his crew come up with the idea to imitate the Sing-Songbird vocalization tricking Hook and his men yet again, giving the real Sing-Songbird time to flee. When Jake and his crew caught 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 Hook 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.
The Sing-Songbird reappears in the episode "Mystery of the Missing Treasure!". Jake and his crew discover that someone has stolen their Team Treasure Chest originally the young pirate believed the thief was Captain Hook and his scurvy band were the thieves but none of the various clues the pirates discover on Pirate Island match Hook and crew. It wasn't until they discover a brown feather and Skully suggest they journey to Buccaneer Bird Bluff to ask their feathered friends if they knew who the feather belongs to. The Sing-Songbird recognizes the feather--it belongs to Fast Claw, the pet falcon of the sneaky, plundering pirate Beatrice Le Beak.