The Wedding Singer
Adam Sandler as Robbie Hart, a 1985 wedding singer dumped at the altar, and Drew Barrymore as the waitress he writes "Grow Old With You" for. The film that proved Sandler could be sweet, and the first pairing of two stars who kept coming back to each other.
The Wedding Singer opened on February 13, 1998, from New Line Cinema, directed by Frank Coraci and written by Tim Herlihy. Sandler had the seed of the idea, a wedding singer left at the altar, and Herlihy, inspired by a radio show called "Lost in the '80s," set it in 1985 and buried it in the decade's texture: a Boy George impersonator, a rap of "Rapper's Delight" by the octogenarian Ellen Albertini Dow, a soundtrack of new wave. Coraci, a friend of Sandler's since NYU, cited John Hughes as his model.
The softer tone was new for Sandler, whose earlier comedies had run on abrasiveness, and Herlihy has credited two things: his own recent marriage, and the chemistry with Drew Barrymore, whom Coraci has called the first and only choice for Julia. Barrymore had approached Sandler about working together, calling them "cinematic soulmates" before they had shared a set, and she did not hear Sandler's songs until the first day they were shot, so her reactions would be real. Carrie Fisher spent six months as a script doctor fleshing out the women's roles; much of her dialogue was later changed back, but Herlihy says her structural work on the second act stayed. Sandler and Herlihy wrote the two originals, "Somebody Kill Me" and the ballad "Grow Old With You."
That second song arrives on a plane to Las Vegas, delivered with an assist from Billy Idol playing himself in first class. Idol, who had no album to promote, said he was "cracking up right from the first couple pages" of the script and liked that his young son could see it; he called the part "a punk rock Cupid." Steve Buscemi's drunken best-man toast, uncredited, became the other set piece critics kept mentioning, even Roger Ebert, who otherwise panned the film.
Made for $18 million, it opened second behind Titanic and finished with $80.2 million domestic and $123.3 million worldwide. Reviews were mixed to warm, with an A-minus CinemaScore from audiences. Two soundtrack albums of new-wave originals followed, then a Broadway musical in 2006, and Sandler and Barrymore reunited for 50 First Dates in 2004 and Blended after that.
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The SNL goofball who became a box-office machine β Billy Madison, Happy Gilmore, The Wedding Singer, The Waterboy. In the '90s his man-child comedies and shouty voices made him one of the most bankable comedians alive.
Happy Gilmore
Adam Sandler as a failed hockey player with a 400-yard running drive and a grandmother in trouble with the IRS β somehow this became a 1996 classic. Christopher McDonald's smug Shooter McGavin, Carl Weathers' one-handed mentor Chubbs, and a Bob Barker brawl that won MTV's Best Fight. You've attempted the Happy Gilmore swing at least once.
The Waterboy
Bobby Boucher, his Mama, Coach Klein, and the Mud Dogs' forty-game losing streak. Adam Sandler's 1998 Cajun football comedy drew some of the worst reviews of his career, opened to a November record anyway, and as of 2020 was still the highest-grossing sports comedy ever made.
50 First Dates
Every morning is Sunday, October 13, and every morning Henry has to make Lucy fall in love with him again. Adam Sandler and Drew Barrymore's Hawaiian reunion gave 2004 the Good Morning Lucy tape, Ten-Second Tom, a walrus named Jocko and 311's reggae-tinged cover of The Cure, and left a trail of remakes from Telugu to Japanese.