Who stars and guest stars in 'Happy Gilmore 2?' In addition to Adam Sandler and his family, the film also stars Julie Bowen, Christopher McDonald, Ben Stiller, Benny Safdie, and B

“Happy Gilmore,” released in 1996, was Sander and Herlihy’s second movie, following “Billy Madison.” Sandler was just exiting “Saturday Night Live.” Herlihy was Sandler’s roommate at New York University and became a lawyer before Sandler got him to stick to writing comedy. (You might remember the “Herlihy Boy” sketch .)