The Sheriff was charged to collect the taxes by Prince John. 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, or taking the single farthing that was in the church's poor box and laughing as he did it. 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 overweight physique. Despite his constant attempts to capture Robin Hood, he always fails. In addition, he is always fooled by Robin Hood's disguises, despite his claims to the contrary. Despite this, he is not stupid, as he was baffled by Prince John's unexpected claim that Robin Hood should be released, and immediately grew suspicious of John' behavior, with his suspicions being confirmed when he found Little John holding the prince hostage via knife-back. The Sheriff commands a posse of archer wolves, and has authority over Trigger and Nutsy. Unlike most Disney villains, the Sheriff is a cheerful character but he seems to have a short temper. He also speaks with a heavy Southern United States accent, which is likewise derived directly from British dialect which most characters speak in.
Later, he is shown traveling though 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 stops 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 sentences 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 to Prince John, he is not above making fun of him when Prince John is not around, as the Sheriff 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 2 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 ignores him, believing he's 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 is 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's unknown how he managed to escape the burning room. 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.
The Sheriff of Nottingham appear in Once Upon a Time, portrayed by Will Traval, as inhabitant of Fairytale Land. Some time 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.
Even though Once Upon a Time was derived directly from Disney films (i.e. Gaston being in this, despite not originating from the original fairytale), the Sheriff was portrayed as a human in this series instead of an anthropomorphic wolf.
The Sheriff makes occasional appearances in the Disney Parks as a meetable character.
- 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 to keep the villainous stereotype of a wolf (since wolves are more stereotypical evil in fiction than goats).
- This character is animated by Milton Erwin Kahl and John Lounsbery.
- In the original Robin Hood story, the Sheriff was the main antagonist, but in the film he is the secondary antagonist.
- 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.
- He is similar to the Wolf Boss from Kung Fu Panda 2. Both are the secondary antagonist, are of the same species, both obey their boss' orders, and both talk back when their master is not around. For instance, the Sheriff makes fun of Prince John when he's not around, while the Wolf Boss mumbles about Shen when he's not around.
- While Robin Hood was in his "old man" disguise and talking to the Sheriff, the Sheriff smiles at the camera.
- Just like his boss, Prince John, the Sheriff abuses his sidekicks (John with Sir Hiss and the Sheriff with Trigger and Nutsy).
- 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 suplot 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.