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After a successful escape, Little John worries about being captured and hanged, and later cites a law against robbing royalty to avoid robbing Prince John. However, he assists Robin in the robbery of Prince John while disguised as a gypsy. While Robin is in the royal coach with the Prince, Little John remains outside and steals gold from a large chest as well as the gold hubcaps of the coach.
Later, in Robin's hideout, he encourages the lovesick Robin to propose to Maid Marian. He then becomes annoyed with Robin for not paying attention when he was supposed to be tending to the fire and says, "Aw man, you burnt the chow!" Then he adds some spices to try to salvage the meal.
At Prince John's archery tournament, Little John, disguised as a nobleman named Sir Reginald, Duke of Chutney, consorts with Prince John. When Robin is captured, he threatens Prince John's life if Robin is not released. Later, in Sherwood Forest, Little John begins playing his song "The Phony King of England" on his lute, and dances with Lady Kluck.
Little John assists in a jail break to rescue the citizens of Nottingham as well as Friar Tuck, who is sentenced to hang at dawn. After Robin retrieves the jail keys, Little John frees all the townspeople. Little John later impersonates the Sheriff to facilitate their escape and pulls a cart containing all the Nottingham residents. When Robin jumps in the moat to escape the castle while the Sheriff's posse shoots at him, Little John and Skippy watch from the forest, believing Robin has been killed.
After King Richard returns, Little John and Robin are pardoned. He drives the coach containing the newlyweds Robin Hood and Maid Marian and allows Skippy to join them.
At the beginning of the House of Mouse theme song, he is inside the entrance talking and laughing with Baloo.
In some episodes, he sits with Robin Hood next to Baloo and Bagheera after a cartoon ends.
In the episode "Dining Goofy", he laughs with Pinocchio at Wilhelmina Packard's joke.
In "Ask Von Drake", he sits at a table with Lady Kluck and a dalmatian pup and is later in the background during "The Ludwig Von Drake Song" when Ludwig von Drake names Lumière and Cogsworth.