- “Uh Oh! Here comes Old Bad News himself... the Honourable Sheriff of Nottingham.”
- ―Alan-A-Dale describing the Sherrif
In contrast to Prince John, who is the mastermind behind the many plans to stop Robin Hood, the Sheriff is a more active antagonist, constantly fighting and attempting to capture Robin Hood. He is completely unsympathetic to the poverty of the town's people, using immoral ways to collect taxes such as forcing out the coins Otto had hidden in his leg cast, regardless of the pain the blacksmith would endure from his broken leg in the process, taking the one farthing Skippy had been given for his birthday and insincerely wishing him a happy birthday, taking money from a blind beggar (who was actually Robin Hood in disguise), or even taking the single farthing that was in the church's poor box and laughing as he did it. He excuses his corruption and cruelty by hypocritically claiming he's only doing his duty. Because of this, he is hated by the people of Nottingham, who often derisively refer to him as "Bushel-britches," referring to the Sheriff's rather obese physique.
Despite his constant attempts to capture Robin Hood, the Sheriff always fails. In addition, he is always fooled by Robin Hood's disguises, despite his claims to the contrary. However, he is not completely stupid, as, following Robin Hood's capture at the archery tournament, he was baffled by Prince John's unexpected claim that Robin should be released, and immediately grew suspicious of John's behavior. His suspicions were confirmed when he found Little John holding the prince hostage by sticking a knife to his back.
Being bigger and heavier than Robin Hood, he physically overpowers him in a fight and Robin has to use his wits to escape him.
The Sheriff puts on a cheerful, friendly act, but is as callous as any Disney villain. He also speaks with a heavy Southern United States accent, which was contrasted with most of the characters who spoke in British accents.
Even if he follows Prince John's orders and claims to be faithful to the Crown, the Sheriff himself seems to not hold a high opinion of the prince, since he happily sings "The Phony King of England" and even encourages Sir Hiss to do the same.
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 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.
The Sheriff of Nottingham, like many others characters created by Disney, appears as a guest character in this series. Some of the episodes that the Sheriff appears in include "The Stolen Cartoons", "Pete's House of Villains", "Goofy's Valentine Date", and Mickey's Magical Christmas: Snowed in at the House of Mouse.
A human version of The Sheriff of Nottingham appears in Once Upon a Time, portrayed by Will Traval as an inhabitant of Fairytale Land. Sometime in the past, Robin Hood humiliated the Sheriff and took the woman he loved, Marian away from him. Later, he meets up with the Dark One, Rumplestiltskin, in the forest. Rumplestiltskin is looking for Robin Hood, and though the Sheriff knows where the man is, he won't give any information. Instead, he proposes Rumplestiltskin allow him to spend a night with his servant, Belle, in exchange for information on the thief's whereabouts. Rumplestiltskin refuses and finds it easier to rip out the Sheriff's tongue as a threat. He tells the Sheriff he'll give it back for information on the thief. Finally, the Sheriff tells him of the deep grudge he holds against the thief, who goes by the name Robin Hood.
After the Curse, his Storybrooke counterpart is Keith, a frequent visitor to The Rabbit Hole bar. One night, he meets a woman, Lacey (Belle becoming amnesiac because a sort launched by The Evil Queen), who is happily playing pool by herself. He assumes she and Mr. Gold (Rumplestiltskin) are no longer together, so he attempts to flirt with her but is quickly turned down.
Later that night, Lacey goes out on a date at the diner with Mr. Gold. She excuses herself to the bathroom to fix her dress but actually goes out to the alley to meet up with Keith. They make out, and Mr. Gold eventually finds them. He angrily pushes Keith off of her thinking she was being forced upon but discovers it was planned. Keith approaches Mr. Gold to apologize stating he did not know they were still a couple, which Mr. Gold bitterly affirms. Mr. Gold has had enough and using magic, he rips out Keith's tongue and hits him with his cane. Lacey is attracted to Mr. Gold's dark side and watches with a mischievous look on her face as he continues to give Keith a continuous brutal beating.
- Unusual for a central character, the Sheriff has no name; he's always called by his title or nickname.
- Nine animations of the Sheriff are reused in the film.
- The character was originally intended to be a stupid goat, but this was dropped by the director who wanted Ken Anderson to keep the villainous stereotype of a wolf (since wolves are more stereotypical evil in fiction than goats, who nonetheless are associated in some cultures with dark magic and demons).
- Coincidentally, in that case, the three villains would have been the three animals that made up the Greek monster Chimera, being a lion, a snake, and a goat.
- This character is animated by Milton Erwin Kahl and John Lounsbery.
- In the original Robin Hood story, the Sheriff is the main antagonist, but in the film, that role is given to Prince John.
- Even though he seems to be fearless, the Sheriff is shown to be afraid of Prince John and obeys his every command, but he still likes to make fun of him by singing the mock song.
- There was a scene deleted from the final film that showed the Sheriff collecting taxes in a tent in the town square. Additionally, the Sheriff was featured in an unused subplot that involved Prince John sending forged love letters to both Maid Marian and Robin Hood in order to lure them into another trap.
- In the alternate ending, the Sheriff was shown crying at Robin and Marian's wedding, indicating that he did not suffer the same fate as Prince John and Sir Hiss at this point, and that, like Nutsy and Trigger, he does his job no matter who he works for.
- In the Norwegian dub, he and Little John are voiced by brothers: Henki and Lasse Kolstad.