Drawing upon the wisdom of great jazz musicians that include Duke Ellington, Miles Davis, Charlie Parker, and John Coltrane, this chapter invites therapists to regard therapy as more like a jazz performance than a psychological or medical intervention. Aphorisms of jazz inspire recommendations for helping make therapy more creatively improvisational. These include honoring and utilizing errors and mistakes, practicing the art of improvisation rather than following predetermined therapy models, bringing rhythm into therapy sessions, evolving one’s own particular therapeutic style, embracing paradox, and making sure that a therapy session, like a jazz performance, makes everyone involved feel more alive. Illustrations of creative therapeutic interventions are included throughout the chapter to demonstrate what is possible when therapists leave models behind to embrace the jazz of creative therapy.