Watched Scream (1996) then all 4 Scary Movies (starting from 2000). I did not plan on the latter, but managed to get a quadrilogy so I thought why not. Since then I learnt there is a 5th episode.
Scary Movie is essentially Scream (a spoof of it) and since Scream isn't frightening at all, I consider it a less funny and more straightforward prototype of Scary Movie, with one less plot twist. I find it fun that around the end of Scream one of the characters say "scary movie", I assume the creators of SM took that as an inspiration. Also Scary Movie took important elements from I Know What You Did Last Summer - which I plan to watch next.
The rest of the Scary Movies are parodies of various horrors and related genres. Lots of stupid shit in them but they are okay.