Watching Your Film Collection

I'm sure many of us here have a massive film collection, whether they're in physical or digital format. I know having a few hundreds isn't huge compare to some people, but there is already enough there, where every time I look, I struggle to choose. I could be sitting there, thinking I want to watch one thing, e.g. a comedy, then I would spot this film I bought last week because I wanted to see that, then one I bought earlier because I saw that when I was a child and haven't seen for a long time, then that box set I bought the other month because it was a 14 film collection with quite a few I want to watch that was for 20 dollars.

How do you go about trying to actually watching everything you've bought?