| The Sheriff appears at the film's opening, sneaking up on Robin Hood and Little John as the two are swimming. Despite his attempts, Robin Hood manages to escape by hiding in a tree.
Later, he is shown traveling through the town for his daily tax collection. He uses several methods to get them. First, he takes them from Otto the blacksmith, by hitting Otto's leg until the coins that the dog hid in his cast come out, which causes obvious pain to Otto's broken leg. At Mother Rabbit's home, he takes the single farthing that was meant as a birthday present for Skippy. The Sheriff even stoops so low as to take money from a blind beggar, while being completely oblivious to the fact that the beggar is Robin Hood in disguise.
The Sheriff is one of the participants in Prince John's archery tournament. Once again, he is unaware of the fact that a stork archer is a disguised Robin Hood. He even carries on a conversation with the "stork" about how Robin Hood did not attend and brags that he could always see through the disguises. Though the sheriff is apparently a decent archer, making it to the final round, he resorts to cheating to defeat the disguised Robin Hood. First, he has his vulture henchman, Nutsy, hide in the target, and the vulture adjusts the target so that the Sheriff gets a bull's-eye. When the "stork" shoots, he nudges the stork's bow, in an attempt to have him miss. He loses anyway, thanks to Robin Hood's skill. After Prince John unmasks Robin Hood and sentenced to beheading, the Sheriff becomes suspicious when the prince suddenly orders Robin to be released. He then discovers Little John holding a knife to the back of Prince John's neck and attacks him, freeing the prince and resulting in the following battle against Robin Hood.
Despite his supposed loyalty, the Sheriff is not above making fun of Prince John when the latter is not around, as he is next seen singing a mocking song about Prince John that the villagers had made up. Later, he presumably imprisons most of the townspeople on the Prince's orders for not paying the dramatically increased taxes that Prince John imposed as punishment for the mockery, takes money from the poor box in the church which is the last straw for Friar Tuck who attacks him, he then arrests Friar Tuck for high treason. On Prince John's orders, he prepares the gallows to hang the Friar, knowing that Robin Hood would no doubt come to stop the execution and lead to his capture. While he and his two vulture henchmen (Trigger and Nutsy) are working, they are approached by a blind beggar, who is once again Robin Hood in disguise. Trigger gets suspicious when the beggar begins asking too many questions about Friar Tuck's execution, but the Sheriff tells Trigger not to worry, as this blind man is harmless.
The Sheriff and his men are then seen guarding the jail, however, the Sheriff had fallen asleep on duty. He gets annoyed by Trigger when his crossbow accidentally fires. When he and Trigger hear the sounds of Nutsy being ambushed by Robin Hood and Little John, they investigate, and find what they believe is only Nutsy, but really Robin Hood. The disguised Robin Hood then puts the Sheriff back to sleep with a lullaby and steals his keys and opens the door to the jail, allowing Little John to enter. When Trigger hears the door shut, he accidentally fires his crossbow again, waking the Sheriff up, who fails to see Little John getting in and then reprimands Trigger for making another false alarm.
Falling back asleep, he has awoken again when coins from one of the bags that was being pulleyed from the royal treasury to a jail cell fell on him. He was then subdued by Little John who stole his clothes to use a disguise to keep Trigger from alerting anyone. The Sheriff is then seen again (in his underwear) chasing Robin Hood when he attempts to escape. The Sheriff corners him in Prince John's chambers and lunges at him with his torch, setting the room on fire. After a brief fight, Robin Hood escapes when the flames cut the Sheriff off from chasing him. It is unknown what happened, but presumably the Sheriff escaped the burning room as well as he is seen alive at the end. The Sheriff is finally seen at the end of the film, having been stripped of his position by King Richard, who returned from the crusades and is sentenced to working in the Royal Rock Pile alongside Prince John and Sir Hiss.
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