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.