Adam Sandler is gearing up to show off his best Tyler Perry skills, as Jack & Jill opens in theaters on Friday.

In the new comedy, directed by Dennis Dugan, Sandler doubles as the lead brother-sister characters, and employs the services of Katie Holmes, Dana Carvey and Al Pacino (who plays himself).

Following a string of small television roles on The Cosby Show, MTV and comedy club appearances, Sandler made his big screen debut in 1989 with Going Overboard, playing cruise ship waiter Shecky Moskowitz.

All my life I just wanted to get on stage and make people laugh, a very young Sandler says in the trailer.

From Going Overboard, the Brooklyn native went on to work on Saturday Night Live for several seasons, before being let go in 1995.

Over the years, Sandler has played some of the funniest and loveable characters in comedy history, including Billy Madison, Robbie Hart, Longfellow Deeds and Chuck Levine.

In 2002, his acting took a more serious turn when he appeared in the Paul Thomas Anderson picture, Punch Drunk Love. His role as funger seller Barry Egan earned Sandler his first (and to date, only) Golden Globe nomination for best actor.

You know what I want to do? I want to actually become, in life, a little more centered and normal, at home, try to be able to just not have to work as much as I do. To just be a normal person, Sandler told Charlie Rose in a 2002 interview.

While Sandler, now 45, is now a husband and father of two, the actor has not fulfilled his wish of working less.

In 2011 alone, he's appeared in three films, Just Go with It with Jennifer Aniston, Zookeeper with Kevin James and the latest, Jack & Jill.

His next comedy is Donny's Boy opposite Andy Samberg, produced under Sandler's company Happy Madison. Sandler is also a producer on the upcoming Richard Pryor biopic.

To celebrate the release of Adam Sandler's latest film, here are his 5 best film roles.

5. Happy Gilmore in Happy Gilmore 1996
Trading in hockey sticks for golf clubs, Sandler made the sport look cool on the big screen. In “Happy Gilmore,” Sandler wore hockey jerseys, shouted “He Shoots, He Scores” on the green, and received much love from Bob Barker (cue punches). “Happy Gilmore” grossed more than $41 million at the box office, and even won an MTV Movie Award for Best Fight between Sandler and Barker. Universal Pictures
4. George Simmons in Funny People 2009
Sandler was part of a big bowl of funny, with help from Seth Rogen, Jonah Hill, Leslie Mann, Jason Schwartzman and director-producer Judd Apatow. In the film, Sandler takes on one of the most serious roles of his career, playing a famous comedian who receives news that has cancer. While “Funny People” received fairly positive reviews, it underperformed at the box office, only making $71 million (the film’s budget was $75 million). Universal Pictures
3. Henry Roth in 50 First Dates 2004
It took six years to reunite Adam Sandler with his “Wedding Singer” co-star Drew Barrymore, but it was worth the wait, as the pair delivered a hilarious romantic comedy packed with aquatic animals, the Hawaiian backdrop and Rob Schneider. Columbia Pictures
2. Barry Egan in Punch Drunk Love 2002
Before “Funny People,” Sandler took a stab at the serious with Paul Thomas Anderson’s “Punch Drunk Love.” The film centers around a lonely salesman who embarks on a whirlwind adventure involving extortion, the love of his life and the wrath of Dean Trumbell, played by Philip Seymour Hoffman. Sandler’s work was recognized with a Golden Globe nomination for best actor that year (he lost to Nicolas Cage). Columbia Pictures
1. Robbie Hart in The Wedding Singer 1998
Billy Idol. Steve Buscemi. The ‘80s. Drew Barrymore. Sandler couldn’t have asked for a better setting when he walked onto the set of “The Wedding Singer” in 1998. Starring as New Jersey wedding singer Robbie Hart, Sandler showed off his music skills on the big screen, belting out classic ‘80s tunes and Adam Sandler originals. The film was a huge success at the box office, as was Sandler’s love song, “Grow Old With You.” New Line Cinema
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