Adam Sandler received critical acclaim for his role in the movie Uncut Gems, which premiered at the Telluride Film Festival on August 30, 2019, and released widely on January 10, 2020. His performance earned him the Independent Spirit Award for Best Male Lead .

Sandler returned to host Saturday Night Live for the first time since leaving the show in 1995. His episode aired on May 4, 2019, and included a tribute to his friend and fellow cast member Chris Farley.

Adam Sandler's Happy Madison Productions signed a four-movie deal with Netflix in October 2014. This deal was later extended due to the success of the films produced under the agreement.

Sandler played both male and female roles in the movie Jack and Jill. Released on November 11, 2011, the film received poor critical reception but was a moderate box office success.

Sandler starred alongside Kevin James in the comedy I Now Pronounce You Chuck & Larry. The film was released on July 20, 2007, and, despite mixed reviews, it was a commercial success.

Sandler took on a more serious role in Paul Thomas Anderson's film Punch-Drunk Love, released on May 19, 2002, showcasing his range as an actor. His performance was widely praised and won him a Golden Globe nomination.

In Big Daddy, Sandler played a man who unofficially adopts a five-year-old boy. The film was released on June 25, 1999, and was a box office hit, further cementing Sandler's successful acting career.

Adam Sandler starred in Billy Madison, which he also co-wrote. The film was released on February 10, 1995, and became a box office success, establishing Sandler as a popular comedy star.

Sandler became a cast member on Saturday Night Live following a recommendation by comedian Dennis Miller. He was a regular on the show from 1990 to 1995, where he gained popularity for characters like Opera Man.