Acting careerIn 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". Early in his career, Sandler performed in comedy clubs, taking the stage at his brother's urging when he was only 17.
He was discovered by comedian Dennis Miller, who caught Sandler's act in Los Angeles. Miller 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, making a name for himself by performing amusing original songs on the show, including "The Chanukah Song". Sandler told Conan O'Brien on The Tonight Show that NBC fired him and Chris Farley from the show in 1995.
Sandler's first starring role was in 1989, in the film Going Overboard. In 1994 he co-starred in Airheads with Brendan Fraser, and Steve Buscemi. He starred in Billy Madison (1995) as a grown, though uneducated, man repeating grades 1–12 to earn back his father's respect, along with the right to inherit his father's multi-million-dollar hotel empire. In At the Movies, Siskel and Ebert gave the film a very bad review, and said of Sandler "...Not an attractive screen presence, he might have a career as a villain or a fall guy or the butt of a joke, but as the protagonist his problem is he creates the fingernails on the blackboard" with Siskel adding "...you don't have a good motivation for the character's behavior". He followed this film with other financially successful comedies such as Bulletproof (1996), Happy Gilmore (1996) and The Wedding Singer (1998). He was initially cast in the bachelor-party-themed comedy/thriller Very Bad Things (1998), but had to back out due to his involvement in The Waterboy (1998) one of his first hits.
Although his earlier films did not receive critical praise, his more recent films, beginning with Punch-Drunk Love (2002), have received more positive reviews. Roger Ebert, in his review of Punch-Drunk Love, concluded that Sandler had been wasted in earlier films with poorly written scripts and characters with no development. Sandler has moved outside the genre of slapstick comedy to take on more serious parts such as the aforementioned Punch-Drunk Love (for which he was nominated for a Golden Globe), Spanglish (2004) and Reign Over Me (2007). He played a loving father figure in Big Daddy (1999). During filming, he met Jacqueline Samantha Titone—his future wife and mother of his two daughters -— who was cast as the waitress from The Blarney Stone Bar.
Collateral (2004). He also was one of the finalists along with Jim Carrey and Johnny Depp for the role of Willy Wonka in Tim Burton's Charlie and the Chocolate Factory (2005). He returned to more dramatic fare with Mike Binder's Reign Over Me (2007), a drama about a man who loses his entire family in 9/11 and rekindles a friendship with his old college roommate (played by Don Cheadle). He starred in the film I Now Pronounce You Chuck and Larry (2007) alongside Kevin James, as a New York City fireman pretending to be gay to keep up an insurance scam so that his best friend's children can have benefits. Sandler headlined You Don't Mess with the Zohan (2008), a comedy about a Mossad agent who fakes his own death and moves to the United States to become a hair stylist. The film was written by Sandler, The 40-Year-Old Virgin writer-director Judd Apatow (who was an old roommate of Sandler's when both were starting out), and Triumph, the Insult Comic Dog creator Robert Smigel, and was directed by Happy Gilmore director Dennis Dugan.
"Like Will Ferrell, Sandler has layers of tenderness under layers of irony under layers of tenderness—plus a floating anger like Jupiter’s great red spot," wrote David Edelstein of New York magazine in a review of You Don't Mess with the Z. "Some performers become stars because we can read them instantly, others—like Sandler—because we never tire of trying to get a fix on them."
Sandler starred in Bedtime Stories (2008), a fantasy film directed by Bringing Down the House director Adam Shankman, about a stressed hotel maintenance worker whose bedtime stories he reads to his niece and nephew begin to come true. This marked Sandler's first family film and first film under the Walt Disney banner. Keri Russell and English comedian Russell Brand co-starred.
In 2009, Sandler starred in Judd Apatow's third directorial feature Funny People. He played a very successful stand up comedian who finds out he has a terminal illness and he takes a young inexperienced comic, played by Seth Rogen, under his wing. Other co-stars included Eric Bana and Apatow's wife, Leslie Mann. The film contained more dramatic elements than Apatow's previous efforts. Filming began in October 2008 and finished in January 2009. The film was released on July 31, 2009. At one point, Sandler was in talks to star in Quentin Tarantino's World War II film Inglourious Basterds, which he confirmed, but he did not appear in it due to a scheduling conflict with Funny People. Following the release of Funny People, it, along with Punch-Drunk Love were cited in the June 2010 announcement that Sandler was one of 135 people (including 20 actors) invited to join the Academy of Motion Picture Arts and Sciences.
Sandler appeared in Grown Ups, teaming up with Kevin James, Chris Rock, Rob Schneider, and David Spade (all of whom have worked with Sandler before) for a film about five best friends from high school who reunite 30 years later on the 4th of July weekend. Other costars include Salma Hayek (playing Sandler's wife), Maria Bello (playing James' wife), and fellow SNL alumna Maya Rudolph (playing Rock's wife), Colin Quinn, Tim Meadows, and Norm MacDonald. Sandler and Dickie Roberts scribe Fred Wolf wrote the script and Dennis Dugan directed the film.
Sandler finished filming Just Go with It with Jennifer Aniston, a romantic comedy written by Allan Loeb and Tim Dowling and directed by Dennis Dugan. He plays a plastic surgeon who asks his office manager, played by Aniston, to pose as his wife in order to prove his honesty to his much younger girlfriend, played by Brooklyn Decker, after telling her he's been married to avoid commitment. Sandler will also provide the voice of a capuchin monkey in Kevin James' Zookeeper, set to be released on July 8, 2011.