I think Little Nicky has more in common with the modern Sandler movies than the 90s ones, but that’d be my second choice for the cutoff. Mr. Deeds is definitely another era
“Anger Management” should have been better, considering it’s probably Jack Nicholson’s goofiest movie that he’s ever done. Something’s just a little off about it.
Anger Management, Little Nicky, and Mr. Deeds are not golden age Sandler, but they are all enjoyable to different extents for what they are. Transitional period stuff. Golden age definitely ends with Big Daddy, which is great
Mr. Deeds was the first Adam Sandler movie I felt was a step down, but You Don’t Mess with the Zohan was the first one I thought was just bad
Watched some interviews with Christopher McDonald. Gotta respect when a character actor embraces the role he is most known for that much. Just chilling having a blast getting invited to celebrity golf tournaments the rest of his life.
Yeah, when Adidas did their Happy Gilmore tie-in apparel a few years ago, he modeled a lot of it and was clearly having a blast.
I’d say the golden age is Billy Madison, Happy Gilmore, The Wedding Singer, The Waterboy, Big Daddy - as these are all widely agreed on as the Sandler classics. After that, there are more debated ones - everyone has their personal favorite post-golden age movie but they aren’t as agreed upon. 50 First Dates is probably the most beloved one of the 21st century
Billy Madison is the best Adam Sandler film. It is just nonstop gags and jokes and it is fully committed to them. Sandler's comedy can be cruel with a lot of punching down, but here it is mostly for fun, like the clown bleeding from the mouth after he fell or the entire O'Doyle family, small children included, being wiped out in an explosion. It rewards paying attention with so many good callbacks, too.
Rewatched Billy Madison. It’s still very funny with several scenes that made me laugh out loud after seeing it 10+ times. It is very heavy on the Sandler voice the first 1/3 but it works for me.