Leigh Botts
Leigh Botts is the main character in the novel and is the teller of his own story through a series of letters and diary entries, most of which are to his favorite author, Boyd Henshaw. When we meet Leigh he is a second-grader with questionable spelling and it not until he reaches sixth grade that we really get to know him properly. Leigh was a happy child whose only problem in life was the fact that the spelling of his name made people think he was a girl. His life changes when he is in fourth grade and he moves to a new town and a new school after his parents are divorced. Leigh is angry but not really old enough yet to understand that he is angry. He lives with his mother who is working alot which means he is often lonely. Leigh is quite shy and although he is friendly he is not the child who makes the first overtures of friendship. He wants to be a writer and is obsessed with the books of Boyd Henshaw.
Leigh feels guilty for being angry with his parents and thinks that it might be his fault that they became unhappy together, because if he had not come along they could still be riding around in his dad's rig together; Leigh misses his father and tries to fill the fatherly void with Mr Henshaw and also Mr Fridley the school custodian, whose company he prefers to the other kids at school.
Leigh is resourceful and single-minded, two characteristics he showed when constructing a burglar alarm for his lunch bag. He is a bright, intelligent child who is beginning to understand the adult world and is not sure if that makes him hAppy, sad or both.
Bonnie Botts
Bonnie is Leigh's mother. She works very hard at her job at a catering company but is ambitious and also takes evening classes three times a week so that she can become a vocational nurse. She has high standards for Leigh and sometimes seems a little hard on him, for example refusing to get the television fixed because she thinks it is bad for his brain. Bonnie married Leigh's father, Bill, when they were both very young but when she grew up they grew apart. She hates living in their old family mobile home but the house she now shares with her son is even smaller with only one bedroom so Bonnie sleeps on the couch. She is keen for Leigh to make friends and encourages his interests, hoping his ambitions will take him somewhere better than where he started.
Bill Botts
Bill is Leigh's father and works as a long-distance truck driver which is why he would be away from home for long periods of time whilst he was still married. Now he lives in a trailer with the family dog, Bandit, and drives agricultural produce all over the country. Bill is an absent father most of the time and rarely remembers to call Leigh when he promises to. Leigh initially believes that this is because his dad doesn't miss him but he does and likely does not call because he does not want to be reminded of the family he doesn't have anymore. Bill is absent for many of the occasions when Leigh most needs his father. Bill does love Bonnie and would like to reconcile but his trucker lifestyle makes that impossible. He is a man of few words and does not express his emotions very well.
Mr Henshaw
Boyd Henshaw is a children's author of note and his books are very popular. He is a pivotal character in the novel although we never meet him in person and all we know about him are the snippets that Leigh includes in his letters; for example Boyd lives in Alaska and two of his novels are about the wildlife that he sees there. He is somewhat encouraging of Leigh's goal to be a writer but always reminding him that he is really too busy to be pen pals with an eleven year old boy. He suggests that Leigh keeps a diary to improve his writing which actually results in Leigh improving not only his style of writing but his understanding of himself as well. According to another character, Angela Badger, Mr Henshaw is a mischievous young man with a twinkle in his eye.
Barry
Barry is Leigh's first real friend at his new school and the first person to ask Leigh home after school. He loves Leigh's house because there are no little sisters there to annoy him like there are at his house. The two boys quickly become inseparable and are often over at each other's houses after school.
Mr Fridley
Mr Fridley is the school custodian and is very kind to Leigh, making him feel special by allowing him to help raise the flag in the schoolyard. It is Mr Fridley who suggests Leigh makes a burglar alarm for his lunch bag and also that he smile more so that people want to be around him.
Angela Badger
Angela Badger is a famous and popular author of children's books that are mostly intended for girls. She gives Leigh an enormous dose of self confidence when she calls him "the author" of the story about riding in his dads rig, and is very constructive in praising his writing.