Well, I recently got a chance to rewatch the Wedding Singer again, and while I was at it, I decided to write down all the songs in order, and when they appear, since I know not all of the songs will be on the two CDs that have been released. Plus it helps to answer those "what was that song" questions that come up. I also decided to add the Billboard rankings for the songs that did rank in the top 40 (I don't have top 100 charts).

Mistakes in the Film

• The most noticable mistake is when Robbie comes over to babysit, and his brother-in-law doesn't want to come to the door because he thinks J.R. might have been shot. The shooting took place at the end of the spring 1980 season. The film states it takes place sometime in 1985.
• The photographer mentions they'll last forever, like "Ivana and Donald, Woody and Mia, and Burt and Loni". Burt and Loni were married from 1988 to 1993. I don't know when the details of their dating became public, but I doubt it was the summer of 1985. Although they did act together in Stroker Ace, which was 1983 so it's not toally unreasonable to think people were starting to associate them as together.
• The other thing I'm unsure about, is when Van Halen announced their breakup. The movie takes place in 1985, the wedding was set for August 5th. I'm pretty sure that it was well known by the summer of 1985 that Sammy Hagar was the replacement singer. Robbie (Adam Sandler's character) tells Linda to get out of his t-shirt or he'll jinx the band and they'll break up. I think by this point they already have.
• Someone mentioned that in the bar scene they are playing the "Blue Monday-88" remix, which would be a definite faux-pas. I listened to it, but it sounds like the regular mix to me. I have both mixes, and while I can tell when listening to the two tracks side by side, the version in the movie doesn't appear to have the extra synth drum beats in it.

Cameo's

• Billy Idol as himself
• Jon Lovitz as another Wedding Singer
• Steve Buscemi as a drunk at the first wedding (and again at the end)

Comments About the Soundtrack

• Volume 2 has two songs that aren't on your list ("Space Age Love Song" by A Flock of Seagulls and "Just Can't Get Enough" by Depeche Mode). Either you missed them or the guys who put together the soundtrack put them on there for no readily explainable reason. They could've put some of the other songs from your list on there. (I counted, there were eleven songs on the list but not either volume of the soundtrack.) Heck, I would've prefered any of those songs over the Flying Lizards' version of "Money (That's What I Want)".

  It's possible I missed them, but I watched and listened pretty closely. I don't think those two songs were in the credits (or played during them) so it's possible they put them in there since they are period pieces. Though, "Just Can't Get Enough" was late 70s, but a Depeche Mode staple well into the 90s. I know the "Valley Girl Soundtrack" did this for their second volume. It's also possible someone mentioned them, but they weren't played.