Saturday Night Live aired its fourteenth season during the 1988 - 1989 television season on NBC. The season began on October 8, 1988, and ended on May 20, 1989. 20 episodes were produced. Before the start of the season, no changes were made to the cast. However, as the season progressed Lorne Michaels would hire two new people to the cast: Mike Myers and Ben Stiller, who joined the show midseason as featured players. Stiller had actually appeared on the show before; his film made it onto the show in the episode hosted by Charlton Heston in 1987.

This season notably saw the second death of an original cast member, Gilda Radner, who died on the day of the season finale from ovarian cancer. In memory of Radner, Steve Martin showed a clip from the famous "Dancing in the Dark" sketch from the 1978 episode hosted by Martin himself as part of his monologue. This was the only season of the show for Stiller. After being on the show for five episodes, Stiller left the show due to creative differences with Michaels.