In the mid to late 1980s, Sandler played Theo Huxtable's friend, Smitty, on The Cosby Show (1987–1988). He was a performer for the MTV game show Remote Control, on which he made appearances as the characters "Trivia Delinquent" or "Stud Boy". Sandler started performing in clubs early on, taking the stage at his brother's urging when he was only 17. He was then discovered by comedian Dennis Miller, who caught Sandler's act in Los Angeles. Miller immediately recommended him to Saturday Night Live producer Lorne Michaels. Sandler was hired as a writer for SNL in 1990 and became a featured player the following year, quickly making a name for himself by performing amusing original songs on the show, including "The Chanukah Song". He left the show in 1995 to focus on his acting career.

Sandler's first starring role was in 1989 when he starred in the movie Going Overboard. In 1995, he starred in Billy Madison, in which he plays a grown, though uneducated, man repeating grades 1–1