Leroy is a concession stand worker with a fierce ambition to become a real cowboy. He wears the requisite hat and boots and carries a lasso, but lacks the essential equine companion. Having reformed from his past as a thief, he approaches life with a desire to do the right thing. He tries to mask his physical insecurities with cowboy slang and an optimistic attitude.

Maybelline is an older horse with only four teeth and a substantial appetite. She is highly sensitive and requires continuous verbal compliments to motivate her movements. She possesses a deep fear of being left alone and relies on affectionate words to feel secure in her environment.

Patty is Maybelline's original owner who seeks a loving home for the animal. She acts as a straightforward instructor to Leroy. She provides him with strict rules for horse care that serve as his primary guidance for animal husbandry.

Beatrice is the ticket seller at the drive-in theater where Leroy works. She acts as the catalyst for his journey by pointing out that real cowboys need horses. She provides him with a newspaper clipping advertising an animal for sale, urging him to take control of his fate.

Mrs. Watson is a cheerful resident of Deckawoo Drive who maintains an exceptionally positive outlook on life. She enjoys eating hot toast with a great deal of butter. She readily welcomes others into her home, operating under the firm belief that there is a way to make anything fit.

Mercy is the Watson family's beloved pet pig. She shares a home on Deckawoo Drive and regularly enjoys eating breakfast with her human family.

Stella is a friendly young girl living on Deckawoo Drive. She is open-minded and eager to interact with newcomers, readily offering kind compliments when she learns it makes others happy.

Frank is Stella's anxious brother who lives on Deckawoo Drive. He approaches new situations with caution and actively worries about his sibling's safety around unknown animals.