Harold
Harold Reynolds (Spencer Breslin) is a 13-year-old boy with early male pattern baldness. Harold seems to cope all right in his hometown, Douglasburg, until his mom, Maureen (Ally Sheedy), announces that the family is moving to a new house in a new town. Harold panics, because he had somewhat fit in with everyone at his old school, despite his baldness.
When he arrives in his new house, Harold is met by an elderly new neighbor, Maude (Suzanne Shepherd), who assumes Harold is older because of his baldness, and starts flirting with him. Harold starts at his new school, and because he initially wears a hat into class, he is seemingly accepted, especially by a girl, Evelyn (Elizabeth Gillies), whom he briefly flirts with. When the teacher, Ms. Vicki Norris (Rachel Dratch), notices him wearing a hat, he is forced to take it off, thus revealing that he is bald. Instantly he is ostracized by the other students, including Evelyn.
Harold's older sister, Shelley (Stella Maeve), has started High School in the new town as an immensely popular and flirty cheerleader. She meets a boy named Patrick (Robert Gorry) and they quickly start dating, which leads to Patrick assuming that Harold is Shelley's father. Patrick asks Harold to buy some beer for him and his friends, which works multiple times.
Harold is bullied relentlessly by students. One of the few nice people is Cromer Styles (Cuba Gooding Jr.), the school janitor. While in gym class, the bullying rears its ugly head and the Coach (Chris Parnell) joins in. Cromer comes to the rescue when he announces Harold is wanted in the office. That was just a decoy – Cromer and Harold watch TV in the janitor's room.
Harold returns home, angry and upset, and decides to go back to his old home, where everyone liked him. He leaves late at night so that his Mom and sister won't get suspicious. He only makes it as far as a strip bar. Harold thinks that because he looks older, he may pass for legal age, but Cromer is there as well, and he takes Harold home. He gives Harold words of encouragement, and then drops him off at home.
The next day in gym class, Harold is asked to take his shirt off as part of the Skins and Shirts team. He has a big strip of hair on his back, and everyone starts laughing at him. He talks to Cromer, and they decide to pull a prank on the coach, turning off the hot water when the coach is in the shower.
Not wanting to go back to school, Harold buys a few beers for himself, and is followed by Maude, who still thinks that he is much older. When he tells her he is 14, she thinks that means the size of his manhood. When he explains he is only 14 years old, she tells him to come back in a few years.
Patrick and his buddies ask Harold for one more favor: to get them some beer for a party. Harold buys the beer, but is arrested by police, who believe him to be an adult selling beer to minors. They do not believe him when he tells them that he is only fourteen. He is taken to jail and is bailed out by Cromer.
Later that night, Patrick apologizes for what happened, and tells Harold he wants to have sex with Harold's sister. Shelley tells Harold she doesn't really want to have sex, although she likes Patrick. They get Cromer to wait outside the hotel room, When Shelley leaves the room, Maude is sent in her place, and Patrick ends up having sex with her.
There is a go cart race coming up, and some of the bullies put a dent in Harold's cart in order to slow him down, but Cromer repairs the dent. A lady from the crowd shows her breasts to the bullies in order to distract them, enabling Harold to win the race, and, ultimately, the respect of the school.
The movie ends with Harold holding his trophy and the bullies apologizing for teasing him, now wanting to be his friends.
revenge, humor