The show was canceled after its first season, but CBS revived it under unusual circumstances. Magnum, P.I. (1980) was ending, leaving CBS with a very expensive lease on an empty Hawaii studio. The producers of this show came up with the idea of the Fat Man retiring from Los Angeles and moving to Hawaii to take up criminal law, with his investigators coming along. He later became District Attorney for Honolulu. The ratings went up sharply with the move. CBS's lease on the Hawaii studio expired during the 1990-91 season, and the show returned to Los Angeles.
William Conrad and Joe Penny were first teamed together in an episode of Matlock, "The Don," in 1986 although they played different characters. Jake and the Fatman introduced the character of Dr. Mark Sloane in an episode in 1991, before Diagnosis Murder began the following season. All three programs were created/produced by Dean Hargrove.
Most of the show's episodes are named after well-known songs from the Swing Era.
The show's second season was delayed by the Writer's Guild strike of spring-summer 1988 and a wildcat strike by resort workers in November 1988. William Conrad arrived in Hawaii incognito and stayed quiet until the second strike was resolved, to avoid charges of conflict of interest.
One of the producers of the series was Fred Silverman, who, when working as a CBS programming executive years before, told Cannon (1971) producer Quinn Martin that a show with a fat lead character would not fly. Of course Cannon did make it to television and was very successful. Both series starred William Conrad.