Trichobezoars or hairballs in the gastrointestinal tract occur as a complication of trichotillomania or compulsive hair pulling, and trichophagia, or compulsive eating of hair. The DSM-5 classifies trichotillomania as an obsessive-compulsive spectrum disorder. In this case series of four children with trichobezoar, we present the varied psychopathology that led to the same and discuss the current literature on complex issues underlying trichotillomania.