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Role in film
Once Prince John's brother, King Richard leaves for the Crusade in Austria, he appoints a new man named Tudlesy to be his own new Sheriff of Nottingham and reveals his true nature and intentions, which is to raise taxes and collect money from the poor in his brother's absence and as long as his mother, Queen Eleanor and the Archbishop of Canterbury remain oblivious to the plot.
Together, they organize an archery contest at the Nottingham fair to determine which archer is the best to serve Prince John and form an army of good arrow shooters under their command. The Sheriff and Prince John seem impressed with a competitor and one of the Sheriff's bowmen, Red Gill's archery skills during the game. As it turns out, it's Lord Hugh Fitzooth and his son, Robin the winners. Nevertheless, knowing the Sheriff's true nature and intentions, both defy and refuse to join and serve him; an act which aspires some other archers to follow Lord Fitzooth's lead. In retaliation, Prince John has the Sheriff send some men to kill them (including Red Gill who killed his father) but they only manage to succeed in killing Robin's father and then getting killed by Robin himself (even Red Gill), thus, begins Robin's life as Robin Hood, an outlaw living in Sherwood Forest who steals from the rich and gives to the poor.
Days later, the Sheriff captures two prisoners: Scathelock, who refused to reveal Robin Hood's whereabouts after the Sheriff stole his cattle since he had no more taxes to pay and Stutely, who was caught poaching a King's deer since the Sheriff starved him, and decides to give them a cruel punishment and torture as a warning to all those who break Prince John's laws. Luckily, Robin Hood and his new band of merrie men, who learned of this affair, storm in to fight off the Sheriff and his men, save the two prisoners, and take them back to Sherwood Forest where they are made new members of his merrie men; leaving the Sheriff and his men to be thrown food at them by the people's revolt; much to Prince John's disgust and chagrin when he arrives at the Square. Angered by this situation, Prince John later consults the Sheriff and sends him and some men to see it that they put an end to Robin Hood and his men at Sherwood Forest.
The next day, the Sheriff and his men ambush Robin Hood and a churchman named Friar Tuck as they are having a duel. Refusing to allow Friar Tuck to finish his business with Robin Hood, the Sheriff and his men attack them; the Sheriff rendering Friar Tuck unconscious during the battle. Outnumbered, Robin calls for his men and they succeed in killing the Sheriff's men and capturing the Sheriff himself, who was being molested at the time by Friar Tuck's dog as he tried to escape.
The Sheriff (blindfolded momentarily) is taken back to Robin's lair by Robin, his men, and the Friar where they force him to eat and drink to the good health of their King Richard, pay the taxes for all the troubles he caused (including the ones he inflicted on his two former prisoners), and later, send him off blindfolded again while riding his horse the other way around back to Nottingham Castle in order to give courage to the poor the Sheriff has persecuted.
Two years have passed, King Richard's Crusade has ended in failure, and the King finds himself imprisoned in Austria to be held for a ransom of 100,000 marks.
The next day, during the donation held by Prince John to avoid his mother and the Archbishop's suspicions since he hadn't actually cared or contributed lately, Maid Marian, the Earl of Huntigdon's daughter, Robin's lifelong playmate, and the Queen's responsibility, presents everyone with Robin Hood and his men's donations; much to Prince John and the Sheriff's chagrin and the Queen and the Archbishop's joy since she disobeyed the Queen and disguised herself as a page. When the Sheriff tries to object on behalf of the Prince, Robin and his men (disguised as peasants) make him pay 1,000 marks; an act which provokes the crowd to ask for as well from him. To avoid embarrassment and suspicion, Prince John has the Sheriff donate as well (1,187 marks) while Robin and his men inconspicuously empty out the rest of the treasury (more than 10,000 marks) into one big chest and present it forth to the donation in front of everyone too, thus, the deliverance of their King is assured; much to the Prince and the Sheriff's shock. After Robin and his men mockingly thank and congratulate the Sheriff for his contribution, they throw him in the river when the Sheriff sees through their disguises and escape.
Refusing to give up all his tax money and to allow his brother to return home safely, Prince John plans to disguise his men as Robin Hood's outlaws to steal his money back tomorrow while the Queen and the Archbishop are conveying the ransom through Sherwood Forest. Knowing Maid Marian has been fraternizing with the outlaws and could see through their deception, thus, jeopardize their plan, Prince John and the Sheriff have her imprisoned in the dungeon and make his mother believe she is with Robin Hood.
After the plan fails to succeed, at night, at the castle, Robin and his men (disguised as Prince John's guards) return and force Prince John and the Sheriff at knife point to take them to Maid Marian and free her. Then, Prince John is thrown in Maid Marian's place in the dungeon by Little John while the others handle the Sheriff.
As the others leave, Robin makes the Sheriff promise to pay their tax money and not to harm them. However, once Robin Hood makes his way out, the Sheriff goes back on his word and blows his cover, thus, a battle ensues; leaving Robin Hood to fight off the guards and the Sheriff. In the end, Robin Hood manages to kill the Sheriff by having him get crushed to death by the closing bridge and then escapes while jumping into the moat. Luckily, Robin's men return to fight off the rest of the Sheriff's archers as they try to hit Robin Hood in the water and rescue.