There's Something About Mary, Kingpin and the Austin Powers movies in the 90's.
Let's be honest here. I loved Adam Sandler on SNL. He was one of my favorites for the group immediately following what was (for me anyways) the greatest SNL group of all time (Hartman, Lovitz, Carvey, Miller, Nealon, Hooks, etc). I think the writing was better and the show had really found its legs. (But, yes, it's hard to argue they were better than Chevy, Murray, Belushi, etc.) Mike Myers came in and then Sandler/Spade and that led into Will Ferrell and so on.
Billy Madison and Happy Gilmore were awesome for somebody who was in college at the time like I was. But we're not exactly talking about transcendent movie comedies. Neither belongs on a list of all-time great comedy movies but they were right place, right time for a big chunk of us who were in Sandler's wheelhouse demographic when they came out. I doubt there are many people born outside say 1968-1978 who are remotely familiar with "Like I got no fucking fingers" or "You button-hooked me" or "Tollbooth Willy" or "At A Medium Pace" or any of the other stuff from Sandman's first comedy album. I just don't know if HG or Billy Madison really stand the test of time. They're great for that group of us who loved them when we were 20 or so. For me, Happy Gilmore 2 was an enjoyable, somewhat nostalgic two hours. It doesn't mean it was a very good movie.