Purpose: Although persistent offenders with histories of imprisonment and violence have disproportionate high rates of psychiatric disorders, little is known of their psychiatric healthcare utilization (HCU) and HCU-associated factors. This study aimed to explore psychiatric HCU, psychiatric morbidity, and psychotropic prescription drugs in violent offenders with a history of incarceration. Methods: Male offenders aged 18–25 (n = 266) imprisoned for violent and/or physical sexual offenses were clinically assessed in 2010–2012 and prospectively followed in Swedish national registries through 2017. Register-based information regarding HCU, psychiatric morbidity, and psychotropic drugs was tracked and compared with a general population group (n = 10,000) and across offending trajectory groups. Baseline risk factors were used to explain prospective psychiatric HCU in violent offenders. Results: Violent offenders used less general healthcare and psychiatric outpatient care, but more psychiatric inpatient care and were more often given psychiatric diagnoses and psychotropic drugs than the general population. Participants previously assigned to persisting offending trajectory groups had higher rates of psychiatric HCU than those assigned to a desisting trajectory. In multivariable regression models, psychiatric HCU was associated with anxiety disorders, prior psychiatric contact, placement in a foster home, psychopathic traits, low intellectual functioning, and persistent offending. Conclusions: Violent offenders are burdened by extensive and serious psychiatric morbidity and typically interact with psychiatric healthcare as inpatients rather than outpatients. Knowledge about their backgrounds, criminal behaviors, and psychiatric statuses can aid the planning of psychiatric services for this troublesome group.