Adam Sandler : Funniest Sandler film?

Big Daddy definitely! This was when Sandler was funny and made some pretty good films. Mr. Deeds was pretty funny too and after that is when he really went downhill. I saw him in Chuck & Larry, Grown Ups and Just Go With It, and he just isn't as funny anymore when he was making films in his early career.

I agree big daddy is his best, funniest and charming

I can watch 50 First Dates over and over again, and laugh every time.

"50 First Dates"

Oh, right... This movie exists! Yeah I must admit, I liked this one as well. This, Happy Gilmore, Anger Management and Mr. Deeds are about the only Sandler's movies that I legitimately enjoyed. Big Daddy actually had its moments, but this kind of childish humour really gets me bored quick.

As for the rest that I've seen (and not seen but the reviews and what people tell me don't inspire me to take a shot), it was honestly all trash. It's always the same humour, the same type of character and plots that are so simple that a 5 years old kid could have written it. Sometimes he even tries to give a dramatic touch (to me mostly unwatchable) which seems to work with the audience in general, but with me, nah.

Reign over Me was generally praised but for me it was and empty movie and no, I didn't think that Sandler nailed it in a dramatic role. I almost wanted to laugh, even though the subject was totally depressing. I just couldn't take his acting seriously. That is me, I don't ask anyone to share my opinion.

I know I still should watch Billy Madison and Drunk-Punch Love as they both seem praised.

Billy Madison and Happy Gilmore