On the first day of high school, Wade and Ryan witness two bullies, Filkins and Ronnie, attack a geek, Emmit, by stuffing him into his locker. Wade intervenes. Filkins and Ronnie begin endlessly targeting Wade, Ryan and Emmit. Emmit also befriends the duo, much to Ryan's dismay.Wade suggests hiring a bodyguard. They place an ad on the Internet, and after a series of disturbing interviews with ex-cons and hired guns, they end up selecting Drillbit Taylor (Owen Wilson). Drillbit pretends to be a martial arts expert and mercenary, but is really a homeless beggar. His real intention of becoming their bodyguard was to rob them and use the money to buy a ticket to Canada. Drillbit tells the boys to find some common interests and become friends with Filkins and Ronnie. Ryan challenges Filkins to a rap battle, but gets carried away and ends up humiliating Filkins. As an angry Filkins, alongside Ronnie, ambushes Wade, Ryan, and Emmit. The boys try using a tactic Drillbit taught them, but it ultimately fails. The boys are furious with Drillbit's teachings. But they decide to bring him to school as a substitute teacher, and in that capacity he is able to protect them. While there, Drillbit meets a teacher, Lisa Zachey (Leslie Mann), and they start a sexual relationship.One morning as his mother is driving him to school, Ronnie sees Drillbit taking a shower at the beach; his mother reveals that he is homeless. Ronnie tells Filkins and Filkins finds the boys and punches Drillbit. Later on, at Wade's house, they catch Drillbit's homeless friends stealing everything in sight, leaving the house completely empty. Drillbit confesses that his real name is Bob and he went AWOL from the U.S. Army and his name was drillbit because he hurt his pinky in high school with a drillbit. The boys fire Drillbit, who later recovers all of Wade's possessions and places them back before Wade's parents return home. Unfortunately, the boys accidentally let slip about Drillbit. Their parents take things up with the principal, who contacts the police. Filkins plays innocent and charms all the adults; Filkins continues to ridicule the boys after Drillbit's disappearance. Tensions finally burst when Filkins interrupts Wade's attempt to ask his crush, Brooke Nguyen, out. Without realizing what he was doing, Wade challenges Filkins to a fight. After Ryan insults Emmit, he refuses to help them.Wade and Ryan arrive at Filkins' house, where he is hosting a party; initially the duo knock him down, but he soon overpowers them. Ronnie shows up to help Filkins against them. Emmit, who has a change of heart, comes to their aid and for a while causes quite a lot of pain to Filkins, and almost defeats him; but Ronnie knocks him out while he is trying to break Filkins' leg. Drillbit shows up and Filkins punches him. Drillbit refuses to fight back until it is revealed Filkins is not a minor (he's 18, therefore, he's not really emancipated). Upon learning this, Drillbit quickly begins fighting and knocks Filkins out cold. He is about to attack Ronnie, but he is spared when he reveals he's only 17. Within minutes, the police arrive and Drillbit flees for fear of prosecution. Filkins wakes up and throws a samurai sword at the boys, but Drillbit catches it. He saves them, at the cost of half of his pinkie finger in the process.Filkins is arrested and shipped off to Hong Kong where he will live with his parents under house arrest until he turns 21 as an alternative to being sent to prison for the attempted murder of the three boys with the sword along with his breaking many underage drinking laws. Another condition of house arrest as opposed to prison is that he is to never attempt to make any contact Wade, Ryan and Emmit ever again. Ronnie reveals that he had been bullied by Filkins several times in an interview with the police, and is cleared of any wrongdoing. Wade, with renewed confidence, asks Brooke out, and she accepts. while Ryan finally accepts Emmit, and declares him a friend. Drillbit is taken to jail, but ends up being released within three weeks. He is reunited with Lisa and the boys.In a post-credits scene, Drillbit is revealed to have become a school nurse and asks a kid with a bloody nose if he needs a bodyguard.
Output: Question: How did Bob hurt his pinky in high school?, Answer: WITH A DRILLBIT