Linda Doucett was fired from the show after the third season. In real life, she and Shandling were in a long-term relationship but they broke up after the third season. Doucett sued Shandling and producer Brad Grey for wrongful termination. The case was settled out of court and Doucett received $1 million.
Shandling based the show on his experience as the Monday night guest host of The Tonight Show Starring Johnny Carson (1962) from 1986 to 1987. Shandling was offered numerous deals to host his own late-night talk show but turned them all down.
Originally, a real studio audience was used for the talk show scenes. But sometimes the scenes would take hours to shoot which was tough on the audience. Eventually, they stopped having an audience unless the episode needed crowd reaction shots. A laugh track was used instead.
The on-air segments were shot on video while the behind-the-scenes segments where shot on film. This required four video cameras and three film cameras shooting simultaneously during the talk show scenes.