Cybill Shepherd and Bruce Willis did not get along during production. Willis' success with Die Hard (1988) further strained their relationship. Willis became a major film star, and bristled at being the second-billed actor on a TV series. He also resented Shepherd, blaming her for many of the shooting delays.
Bruce Willis made the film Die Hard (1988) while starring in "Moonlighting." By the time the series ended, "Die Hard" was available on VHS. In one of the last "Moonlighting" episodes, Willis and a love interest are seen walking past a video rental store while an employee is tearing a "Die Hard" poster down from the window.
At various times throughout the series, actors would looked directly into the camera and talk to the audience. The dialogue mentioned the producers, director, writers, and/or script. In the second-season finale, the characters left the set and ran around the studio.
The most expensive series on TV at the time, with an average cost of $1.6 million per episode. ABC was willing to spend the money because the network owned the show, making more profit than if the series was owned by a separate production company.
Many episodes included a shot of Maddie's feet stepping off of the elevator and walking to her office. Glenn Gordon Caron admitted that the shots existed to give him time to complete the script. Scripts were constantly re-written, and shooting often began without a completed script. Caron would continue writing while shots of Maddie's feet were set up and filmed.
Episodes were shot in 12 to 14 days, much longer than the usual 7 days for an hour-long series. Dialogue was often written only hours before shooting. Scenes were sometimes filmed days before airing. Because of the delays, the series never reached the usual 26 episodes per season. Only 66 episodes were produced from 1985-89.
The third season became notorious for repeated delays of new episodes and a large number of "filler" episodes that ignored the primary story arc, including: a Christmas story, a retrospective show, a Shakespeare spoof, and an episode focused on Miss DiPesto. The scheduling problems happened because Bruce Willis broke his shoulder skiing, and Cybill Shepherd was pregnant with twins. One episode starts with a mock newsreel announcing the behind-the-scenes problems.
Glenn Gordon Caron was hired away from Remington Steele (1982), another series about a pair of bickering detectives, to create and produce this show. He left after the third season due to the chaotic production and disagreements with Cybill Shepherd.