After inheriting a controlling interest in his great uncle's media corporation, Longfellow Deeds (Adam Sandler), a small town pizza store owner, travels to New York City to wait for a deal to be put in place for him to sell his shares for forty billion dollars. While his great uncle's lawyer (Peter Gallagher) works out a plan to cheat Deeds out of his fortune, tabloid reporter Babe Bennett (Winona Ryder) cozies up to the good-hearted heir in order to uncover some dirt. But, when Babe falls for Deeds, she'll have to explain her actions when he discovers her true identity. Directed by Steven Brill. With John Turturro, Allen Covert and Erick Avari. Categories: Comedy, Romance. Year: 2002.

Adam Sandler in Mr. Deeds
Barry Egan (Adam Sandler) owns and operates a small business distributing novelty toilet plungers. Socially impaired and lacking self-esteem, Barry contacts a phone sex operator, who then threatens him with blackmail. When Barry doesn't cooperate, the operator sends some thugs on a mission to extort him. Barry is desperate until one of his seven sisters fixes him up with a lovely English woman named Lena (Emily Watson). With his emotions going haywire, Barry decides to do whatever it takes to get his shot at true romance. Directed by Paul Thomas Anderson. With Philip Seymour Hoffman and Luis Guzmán. Categories: Comedy, Drama, Romance. Year: 2002.

Adam Sandler in Punch-Drunk Love
Little Nicky (Adam Sandler), a kind-hearted demon who has an angel for a mother (Reese Witherspoon) and the Devil as a father (Harvey Keitel), leaves his home in Hell to stop his evil brothers Adrian (Rhys Ifans) and Cassius (Tommy 'Tiny' Lister) from wreaking havoc on the unsuspecting citizens of New York City. With the gates of Hell frozen over and the Devil disintegrating from the lack of new souls, Nicky has one week to find a way to get his brothers home, or neither Hell nor Earth will never be the same. Directed by Steven Brill. With Allen Covert, Peter Dante and Robert Smigel. Categories: Comedy, Fantasy, Romance. Year: 2000.

Adam Sandler in Little Nicky
After receiving a large settlement following a car accident, law school graduate, Sonny Koufax (Adam Sandler) gave in to his slacker nature and settled into an easy life working in a toll booth. When child services shows up at his door one day and drops off Julian (Cole Sprouse and Dylan Sprouse), the five-year-old son of his roomate Kevin (Jon Stewart), who happens to be on a business trip to China, Sonny doesn't know what to do. Eventually, he decides that he can use Julian to win back his ex-girlfriend (Kristy Swanson), who left him because of his lack of motivation and immaturity. While Sonny and Julian initially struggle with their awkward new realtionship, ultimately Julian helps Sonny accept the responsibilities of adulthood and Sonny provides Julian with the loving father he's never had. Directed by Dennis Dugan. With Joey Lauren Adams, Leslie Mann, Allen Covert and Rob Schneider. Categories: Comedy. Year: 1999.

Adam Sandler in Big Daddy
Bobby Boucher (Adam Sandler), a sheltered young man from the Louisiana swamps with a stutter and an unnatural love for water, finds the perfect fit for his talents when he becomes the waterboy for a horrible college football team. When Coach Klein (Henry Winkler) discovers Bobby's amazing tackling skills, he recruits the simple young man to turn his team around. But, in order to keep his dream of attending college alive, Bobby will have to hide his new activities from his overbearing mother (Kathy Bates). Directed by Frank Coraci. With Fairuza Balk, Jerry Reed and Rob Schneider. Categories: Comedy, Sports. Year: 1998.

Adam Sandler in The Waterboy
Robbie Hart (Adam Sandler), a popular wedding singer, takes pride in turning happy couples' special days into all out '80s celebrations. But, when his fiancee Linda (Angela Featherstone) leaves him at the alter, Robbie becomes an inconsolable, drunken mess. Things start to turn around when Robbie meets Julia (Drew Barrymore), a fun, warm-hearted waitress, but just as he realizes he has feelings for her Julia elopes with a man who doesn't appreciate her. Unwilling to let Julia go, Robbie gives chase to tell her how he feels before it's too late. Directed by Frank Coraci. With Christine Taylor, Allen Covert, Steve Buscemi, Jon Lovitz and Matthew Glave. Categories: Comedy, Romance, Music. Year: 1998.

Adam Sandler in The Wedding Singer
Happy Gilmore (Adam Sandler), a failed hockey player, takes his powerful drive to the PGA tour in order to save his grandmother's (Frances Bay) home. Accustomed to the aggresion and bravado of hockey, Happy shows his emotions on the fairway, and quickly becomes a fan favorite. But, as his skills improve, long-time pro Shooter McGavin (Christopher McDonald) begins to see Happy as a threat to his quest for the tour championship, and sets out to squash Happy and preserve the sanctity of the game. Directed by Dennis Dugan. With Julie Bowen, Carl Weathers, Allen Covert, Bob Barker, Kevin Nealon and Ben Stiller. Categories: Comedy, Sports. Year: 1996.

Adam Sandler in Happy Gilmore
In order to inherit his father's (Darren McGavin) hotel empire, spoiled, immature slacker Billy Madison (Adam Sandler) must repeat every grade in school - his father bribed all of his teachers the first time - in order to prove himself worthy. Billy feels right at home in elementary school and becomes the most popular guy in class. But, as he enters high school, he begins to feel the pressure and experiences the same type of ridicule that he used to dish out. To make matters worse, Billy must also deal with interference from his nemisis, Eric Gordon (Bradley Whitford), who stands to gain control of the company should Billy flunk his final test. Directed by Tamra Davis. With Bridgette Wilson, Josh Mostel, Norm MacDonald, Mark Beltzman and Larry Hankin. Categories: Comedy, Romance. Year: 1995.

Adam Sandler in Billy Madison
Tired of struggling for success, Chazz (Brendan Fraser), Rex (Steve Buscemi) and Pip (Adam Sandler), the three members of the rock bank The Lone Rangers, decide to break into a local radio station to have their demo played. When their plan backfires and their demo is accidentally destroyed, the band panics and takes the station hostage with a bunch of water guns. With the police outside, Chazz and his friends find an unlikely ally in Ian (Joe Mantegna), a popular DJ, and eventually a hoard of rock fans descend on the station, demanding to hear the band's music. Directed by: Michael Lehmann. With: Chris Farley, Michael McKean, Judd Nelson, Ernie Hudson, David Arquette, Reg E. Cathey and Michael Richards. Category: Comedy, Music, Crime. Year: 1994.

Adam Sandler in Airheads