This episode was likely inspired by the real-life story of Beach Boy member Brian Wilson and his therapist Eugene Landy. Under the guise of comprehensive, 24/7 therapeutic guidance, Landy took control of Brian Wilson's life. He closely controlled who he interacted with, over-medicated him, managed his career, and even helped publish a Brian Wilson autobiography that described Landy very favorably (the biography has since been universally disregarded for its inaccurate portrayal and blatant plagiarism of previous works). Wilson was eventually able to be released from Landy's care with the help of his wife (then girlfriend) Melissa Ledbetter. Landy's professional license was revoked by the state of California and he was barred from making any more contact with Brian Wilson.
Guest star Michael A. Ross (playing Eddie Devon) is the real-life husband of series cast member Markie Post.
Denise and Dian Gallup also played 'Doublemint Twins' in commercials for Doublemint Gum. Bull's poem about the twins begins "Double your pleasure, double your fun...", which is the beginning of the Doublemint Gum slogan.
Stuart Pankin who plays Dr. Charles Melnick and John Larroquette would go on to star together in the movie Second Sight (1989).
The title comes from the song "Up on the Roof" written by Gerry Goffin and Carole King, notably recorded by The Drifters and James Taylor.