The faults, and they are numerous, can probably be summed up as a case of poor design. The Wedding Singer really can't decide what it wants to be. Is it a romantic comedy? An 80s period piece, or a vehicle to show Adam Sandler's comic ability? Who knows? Not the producer, not the director, and certainly not the audience.
The story is a pretty silly tale about a guy named Robbie who has no ambition other than to be a nice guy. He lives in his sister's basement while etching out a pitiful living as a wedding singer and that's okay with him. The opening scenes go to great length to show us just how nice this guy is. He smoothes the feathers that Steve Buscemi brilliantly ruffles, and then saves an intoxicated pre-teen from sharing his shame with his family. So we quickly get the picture, Robbie is a real sweetie.
He thinks he's getting married, but at the last minute, the broad backs out on him. It's all pretty lame, but it serves as a vehicle to carry us from the soppy beginning of the movie to the middle, which evolves like a dime novel romance between Sandler and Drew Barrymore. It's all very apparent that we are going to go through the boy meets girls loses girl almost gets girl then finally woes her in a big production number at the end. So toss out the story as something to attract your interest, because there's nothing meaty there at all.
So what's left is a clumsy glut of 80s popular culture stereotypes or impersonations, which are never funny, and quickly become irritating. Christine Taylor's material girl is as sickening as Allen Covert's Michael Jackonisms. Crowning all this rot is the whole Boy George scenario, which has neither rhyme nor reason.
I guess that leaves the music. From Adam Ant to Billy Idol there are lots of songs that regurgitate the recent past with a fondness that only those of us who loved that stuff can effect.
Overall this movie is an indecisive thing. If its a love story it's one that we've seen ad nauseum. And if it's a period piece then it's a poor attempt to recreate the 80s. So The Wedding Singer is best described as a lame duck that fits nowhere and does nothing. The real surprize is that there are actually enjoyable moments embedded in this nonesence such that the overall movie going experience is nowhere near as painful as you might imagine. This film is helpless fairy floss, but it's okay.