Sandler proved the commercial success of the critically panned "Billy Madison" was no fluke by co-writing another low-brow starring vehicle, the golfing comedy "Happy Gilmore" (1996), which took in more than $40 million. Adding further proof of his box-office appeal, that year's "Bulletproof", teaming him with Damon Wayans, opened at Number 1, but none of these coups prepared anyone for the breakout phenomena of "The Wedding Singer" (1998), a relatively sophisticated product (by Sandler's standards) which grossed $80 million and finally brought women to the ranks of what had previously been his male fan base. He reverted to his classic outsider image for "The Waterboy" (also 1998), its $39 million opening weekend flying in the face of conventional wisdom saying moviegoers prefer more serious fare in the fall. With everyone calling him the heir-apparent to Jim Carrey's low-comedy throne, Sandler, whose underdog quality and vulnerability separates him from his comic peers, headlined "Big Daddy" (1999), as a slacker who adopts a boy to win back his girlfriend. The film had more heart than "The Waterboy" and while it was not as overwhelmingly succesful, it did register as another solid hit for Sandler. While helping fellow SNL alumnis out by producing their comedies ("Joe Dirt" for David Spade in 2001 and "The Animal" for Rob Schneider, also in 2001) he put out the mediocre comedy "Little Nicky" in 2001. He followed up with "Mr. Deeds" in 2002 which also performed poorly, suggesting maybe Sandler's golden touch was beginning to tarnish.

Perhaps sensing the need for a change of direction, Sandler starred opposite Emily Watson in the critically acclaimed dramatic comedy "Punch-Drunk Love" (2002) which premiered at Cannes and took home The Golden Palm award there. Taking on a more mature role in the romantic comedy created expressly for him by writer-director Paul Thomas Anderson, Sandler successfully built upon his likeable sad-sack persona and added darker edges in a more true-to-life scenario. The new dimension impressed both critics and moviegoers. In 2003, Sandler joined Jack Nicholson as the unlikely pair took on the roles of patient and therapist in the clever David Dorfman comedy "Anger Management," with Sandler's uptight, rage-repressed everyman serving as the perfect foil for Nicholson's wild-eyed, unshaven and slightly psycho psychotherapist.

Sandler reunited with his "Wedding Singer" co-star Barrymore for "50 First Dates" (2004), a romantic comedy that cast Sandler as Henry Roth, a man who falls in love with a woman with a disorder that eliminates her short-term memory and forces him to woo her anew each and every day. The actor was better served in his next project, writer-director James L. Brooks' "Spanglish" (2004), playing a chef grappling with the challenges of his out-of-control wife (Tea Leoni) and the emotional damage she inflicts on their daughter, even as he is attracted to the beautiful and sensitive maid who doesn't speak English (Paz Vega). The film's serio-comic tone did not work for everyone, but Roger Ebert summed up the opinion of most critics when he said of Sandler's performance that he likes Adam Sandler most when he's not in typical Adam Sandler movies. The actor delivered another sweet and sensitive portrayal suggesting that he, if not all of his fans, had evolved away from the wacky, "dumb guy" comedies that made him a superstar. His remake of prison football comedy "The Longest Yard" (2005)--with Sandler in the Burt Reynolds role of a jailed NFL quarterback leading a team of inmates against their guards--was a half-step backward: although missing much of the original's charm and edge, it proved popular at the box office.

-taken from Yahoo Movies-