Trent,try this.It worked for me.List your top 100 on a sheet of paper,then begin to reduce it by any number you like,maybe 5 or 10 at a time till you get your top 10 favorites,.
Be honest with yourself.Do you really like this one better than another.When you first start,it will be difflicut,but as you reduce the number,a pattern will take shape.
You actually might find yourself choosing a genre,or directors.
For instance,I like Epics,like "Bridge on the River Kiwi",and "Lawrence of Arabia",even "Cleopatra".I also like Films by Ridley Scott("Alien"),but not"Blade Runner".And Cleopatra wouldn't make my top 75.
And believe it or not some of my favorites are Black and white films like "To Kill a Mockingbird",and " Twelve Angry Men" with Henry Fonda,and Lee J.Cobb.
I will give you one more.I love the Universal Horror films of the 30's ( Frankenstein""The Mummy",and"Dracula",but I'm not a big fan of Freddie Kruger slasher type films.No imagination,if you get my point.