Chronic daily headaches are an increasingly recognized neurologic issue in children. Frequent headaches can be a source of significant disability and family discord with work/school absenteeism. Medication overuse and emotional disorder would significantly impact treatment and progression. This study examined the frequency of emotional and behavioral problems in children and adolescents with chronic daily headache compared with age-related healthy controls. Prevalence of medication overuse in this chronic daily headache group was evaluated. Otherwise healthy children and adolescents with chronic daily headache (according to International Classification of Headache Disorders-II criteria) were enrolled from the Headache Clinic. Healthy controls were prospectively enrolled from physician offices. Multiple psychological rating scales, headache diaries, presence of medication overuse, and disability surveys (Pediatric Migraine Disability Assessment Survey) were completed. A total of 57 healthy controls and 70 patients were studied. The sample consisted largely of females, many of whom (60%) had medication overuse before medical treatment. Headache patients had significantly more symptoms of anxiety, depression, and somatization compared with controls. Patients with chronic daily headache were at higher risk for emotional disorders, and medication overuse was a significant occurrence, suggesting a need for multisystem treatment approach.