5 Lenny Feder
The only character Adam Sandler has played more than once, other than his recurring TV roles, is Lenny Feder. He’s the central character in 2010’s “Grown Ups” and its sequel, “Grown Ups 2” of 2013. Sandler plays Feder as a family man whose nostalgic memories of fun with his friends can be relived in the present. Starring opposite Kevin James, David Spade and Chris Rock, Sandler is the comic center of both movies.
4 George Simmons
One of Adam Sandler’s best characters is a loosely veiled version of himself. In Judd Apatow’s “Funny People” of 2009, Sandler plays George Simmons, an aging comedy star with a string of mindless movies behind him and a very real illness staring down his future. Forced to reevaluate his life, George reaches out to mend the relationships he’s damaged and to forge new ones. The movie is a survey of all the kinds of funny people in the world, of which the Adam Sandler-type is a crucial one.
3 Henry Roth
In 2004, Adam Sandler added yet another dimension to his acting, taking on the character of Henry Roth in “50 First Dates.” Playing opposite Drew Barrymore, Sandler plays a man whose fear of commitment keeps him from falling in love. The character is sweet and far less crass than the characters Sandler had been known for at the time. The movie is a straightforward romantic comedy, reaching out to new fans without leaving regular Sandler viewers behind.
2 Happy Gilmore
In 1996, Adam Sandler starred in his first major post-“Saturday Night Live” starring role as the title character in the golf comedy “Happy Gilmore.” Sandler also co-wrote the script, so it’s no surprise that the funny dialogue flows out of his character’s mouth so naturally. Happy is a washed-up hockey wannabe who discovers his golf stroke, with some help from a team that includes an eccentric coach, a beautiful love interest and his grandma.
1 Barry Egan
Adam Sandler’s best, most complex role is not his most outwardly funny. In director P.T. Anderson’s “Punch-Drunk Love” from 2002, Sandler plays Barry Egan, a lonely entrepreneur with a host of personal problems. Barry starts out as a sad man audiences can pity. But through quirky determination, he grows into a more honest, more funny character, ready to take the next step toward happiness. The role was a major departure for Sandler, but shows off his range and his ability to insert funny moments into any on-screen story.