So here’s how I try to do this: I usually set the ranking within 24 hours of seeing the movie. This way it’s still fresh in my mind, and I’m giving a good “gut reaction” rating. Also I don’t read any other reviews of a film before I rank it – don’t want to be unduly influenced.
How does a movie earn it’s ranking? What makes a movie highly ranked? Simple: the film has to do what it’s supposed to, and do it well. If it’s a comedy, make me laugh. If it’s a psychological drama, draw me in and keep me guessing until the end, and then make me need to watch the film again.
The ranking I give is the impression I had at the time. Was Gladiator (which I gave a 9) a better film than Primal Fear or The Sixth Sense (both 8’s)? No way. Looking back, both of those films are head and shoulders above the supposed “best picture” of 2000. But that’s not how I felt right after seeing it, so the ranking sticks. In retrospect, I think Gladiator was a generous 7, but I was obviously mightily impressed by something after first viewing it.
Also, personal preference for a particular genre plays a role, as does anticipation. I had very high hopes for Artificial Intelligence: AI, and while a 7 is decent enough, it probably would’ve garnered an 8 or 9 if I hadn’t been expecting so much more. On the flip side, when I saw Save the Last Dance (8 rank), I expected a typical cliché-ridden film, lots of urban strife and the poor white girl trying to fight her way through it all. What I got was an amazing, challenging film that almost seems to go out of its way to set up clichés, just so it can avoid using them. In retrospect, this should probably have gotten a 9.
An important distinction is where the movie was screened. This especially true in the case of comedies, where the laughter of a theater crowd is so infectious. I gave Monsters, Inc. a 9 (one full point of that going to the terrific For The Birds short that was shown in front of it). I stand by that ranking. It was a terrific, fun, heartwarming film. But if I watched it at home, it probably would have garnered an 8, simply because funny films are funnier when seen with an appreciative audience.
I try not to judge based on budget or experience. As long as you make the best of what you’ve got, a low-budget short like Troops can sit at the top of the heap with a 10 (of course, in that example, a cameo by Tom Servo gave it at least 2 bonus points). 
What I like:
It’s odd…I use humor so much in my daily life, but I’d much prefer to watch drama over comedy. Don’t get me wrong – there are a ton of brilliant comedies out there that I absolutely love, but given my druthers, I prefer a flick that gives me something to think about. That’s the hallmark of a great movie to me. If a film sticks with me for days after viewing, and I just can’t get questions or observations about it out of my head, then the filmmakers did their job.
Comedy generally doesn’t afford that. You watch, you enjoy, you laugh, you leave. A few jokes will stick with you, and you’ll get a chuckle out of them for a few days. But this isn’t a flaw, it’s just the nature of the genre. The same with romantic comedy. Just about every one of these films on my list got a 7, simply because they’re very formulaic (and daaamn, there’s a lot of 'em…can you tell what kind of films my wife likes to rent? :)). It might be harder to make a very bad romantic comedy than it would to make an exceptionally good one. “Boy gets girl, boy loses girl, boy gets girl back, they live happily ever after” is a formula that works, and it’s critic-proof. Are any of these “great movies”? No, but they’re not trying to be. The idea is to turn your brain off for 90 minutes and just let the film wash over you. Is Serendipity in any way a “good movie”? Not at all, but I watched it with someone I was in love with, was highly entertained by it, and I’m not about to go and ruin the experience by thinking further about a movie that would collapse if you look at it too hard. The Usual Suspects, The Sixth Sense, Memento, these are films that demand thought. Films like Serendipity, which are good for what they are, certainly do not.
Cripes – when I get on a roll about movies…
Anyway, enough blathering – here’s the list:
American History X (1998) 10
Lord of the Rings: The Fellowship of the Ring, The (2001) 10
Shawshank Redemption, The (1994) 10
Silence of the Lambs, The (1991) 10
Star Wars (1977) 10
Star Wars: Episode V - The Empire Strikes Back (1980) 10
Troops (1998) 10
Usual Suspects, The (1995) 10
Breakfast Club, The (1985) 9
Chasing Amy (1997) 9
Clerks. (1994) 9
Ed Wood (1994) 9
Frequency (2000) 9
Fugitive, The (1993) 9
Get Shorty (1995) 9
Gladiator (2000) 9
Green Mile, The (1999) 9
Harry Potter and the Chamber of Secrets (2002) 9
Harry Potter and the Sorcerer’s Stone (2001) 9
Jaws (1975) 9
Matrix, The (1999) 9
Memento (2000) 9
Minority Report (2002) 9
Monsters, Inc. (2001) 9
Mystery Science Theater 3000: The Movie (1996) 9
One Flew Over the Cuckoo’s Nest (1975) 9
Princess Bride, The (1987) 9
Pulp Fiction (1994) 9
Raiders of the Lost Ark (1981) 9
Red Dragon (2002) 9
Reservoir Dogs (1992) 9
Scared Straight! (1978) 9
Schindler’s List (1993) 9
Se7en (1995) 9
Shakespeare in Love (1998) 9
So I Married an Axe Murderer (1993) 9
Star Wars: Episode II - Attack of the Clones (2002) 9
Star Wars: Episode VI - Return of the Jedi (1983) 9
To Kill a Mockingbird (1962) 9
Toy Story 2 (1999) 9
Wo hu cang long (2000) 9
“Stand, The” (1994) (mini) 8
8 Mile (2002) 8
Basic (2003) 8
Being John Malkovich (1999) 8
Bowling for Columbine (2002) 8
Close Encounters of the Third Kind (1977) 8
Crow, The (1994) 8
Donnie Darko (2001) 8
Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964) 8
Erin Brockovich (2000) 8
Fight Club (1999) 8
Final Destination (2000) 8
Final Fantasy: The Spirits Within (2001) 8
Finding Forrester (2000) 8
Finding Nemo (2003) 8
Ghost World (2000) 8
Groundhog Day (1993) 8
Hannibal (2001) 8
Heartbreakers (2001) 8
High Fidelity (2000) 8
Jay and Silent Bob Strike Back (2001) 8
Jerk, The (1979) 8
Jurassic Park (1993) 8
K-PAX (2001) 8
Letter From Death Row, A (1998) 8
Lilo & Stitch (2002) 8
Man on the Moon (1999) 8
Man with Rain in His Shoes, The (1998) 8
Manhunter (1986) 8
Men in Black (1997) 8
Monty Python and the Holy Grail (1975) 8
Murder in the First (1995) 8
Negotiator, The (1998) 8
Ocean’s Eleven (2001) 8
Office Space (1999) 8
One Hour Photo (2002) 8
Pirates of the Caribbean: The Curse of the Black Pearl (2003) 8
Primal Fear (1996) 8
Ring, The (2002) 8
Royal Tenenbaums, The (2001) 8
Save the Last Dance (2001) 8
Scared Straight! 20 Years Later (1999) (TV) 8
Shrek (2001) 8
Signs (2002) 8
Sixth Sense, The (1999) 8
Star Wars: Episode I - The Phantom Menace (1999) 8
Stir of Echoes (1999) 8
Total Recall (1990) 8
Training Day (2001) 8
U.S. Marshals (1998) 8
Unbreakable (2000) 8
15 Minutes (2001) 7
About a Boy (2002) 7
Airport (1970) 7
America’s Sweethearts (2001) 7
Analyze This (1999) 7
Artificial Intelligence: AI (2001) 7
As Good As It Gets (1997) 7
Best in Show (2000) 7
Birdcage, The (1996) 7
Bowfinger (1999) 7
Boys Don’t Cry (1999) 7
Bruce Almighty (2003) 7
Changing Lanes (2002) 7
City of Angels (1998) 7
Dark City (1998) 7
Dirty Dancing (1987) 7
Domestic Disturbance (2001) 7
Don’t Say a Word (2001) 7
Emperor’s New Groove, The (2000) 7
Enemy at the Gates (2001) 7
Enough (2002) 7
Evolution (2001) 7
Final Destination 2 (2003) 7
Frailty (2001) 7
Ice Age (2002) 7
Identity (2003) 7
Importance of Being Earnest, The (2002) 7
Jerry Maguire (1996) 7
Jurassic Park III (2001) 7
Keeping the Faith (2000) 7
Lost World: Jurassic Park, The (1997) 7
Martha, Meet Frank, Daniel and Laurence (1998) 7
Men of Honor (2000) 7
Mumford (1999) 7
My Big Fat Greek Wedding (2002) 7
Narc (2002) 7
Nemesis Game (2003) 7
Notting Hill (1999) 7
Payback (1999) 7
Phone Booth (2002) 7
Planet of the Apes (2001) 7
Proof of Life (2000) 7
Punch-Drunk Love (2002) 7
Pushing Tin (1999) 7
Rules of Engagement (2000) 7
Rush Hour (1998) 7
Rush Hour 2 (2001) 7
Serendipity (2001) 7
Shallow Hal (2001) 7
Simple Plan, A (1998) 7
Spider-Man (2002) 7
Stuart Little (1999) 7
Two Weeks Notice (2002) 7
Vulgar (2000) 7
Walk to Remember, A (2002) 7
Watcher, The (2000) 7
Wedding Singer, The (1998) 7
What Lies Beneath (2000) 7
What Women Want (2000) 7
Where the Heart Is (2000) 7
10 Things I Hate About You (1999) 6
Angel Eyes (2001) 6
Bachelor, The (1999) 6
Beautiful (2000) 6
Bringing Down the House (2003) 6
City by the Sea (2002) 6
Deliver Us from Eva (2003) 6
Dragonfly (2002) 6
Family Man, The (2000) 6
Fools Rush In (1997) 6
Get Over It (2001) 6
High Crimes (2002) 6
Hollywood Homicide (2003) 6
How to Lose a Guy in 10 Days (2003) 6
Hunted, The (2003) 6
Jackal, The (1997) 6
Lucky Numbers (2000) 6
Maid in Manhattan (2002) 6
Men in Black II (2002) 6
Mexican, The (2001) 6
Miss Congeniality (2000) 6
Murder by Numbers (2002) 6
Next Best Thing, The (2000) 6
One, The (2001/I) 6
Orange County (2002) 6
Osmosis Jones (2001) 6
Other Sister, The (1999) 6
Pay It Forward (2000) 6
Pearl Harbor (2001) 6
Pitch Black (2000) 6
Pledge, The (2001) 6
Quiet Man, The (1952) 6
Runaway Bride (1999) 6
S.W.A.T. (2003) 6
Siege, The (1998) 6
Trapped (2002) 6
Anger Management (2003) 5
Autumn in New York (2000) 5
Banger Sisters, The (2002) 5
Below (2002) 5
Down to You (2000) 5
Drive Me Crazy (1999) 5
Duets (2000) 5
Glass House, The (2001/I) 5
Here on Earth (2000) 5
I’ve Been Waiting for You (1998) (TV) 5
Random Hearts (1999) 5
Say It Isn’t So (2001) 5
Someone Like You… (2001) 5
Sweet Home Alabama (2002) 5
Valentine (2001) 5
Dr. Dolittle 2 (2001) 4
Dungeons & Dragons (2000) 4
Sugar & Spice (2001) 4
Wedding Planner, The (2001) 4
Dr. T & the Women (2000) 3
Godzilla (1998) 3
Nine Months (1995) 3
Plan 9 from Outer Space (1959) 3
Sweet November (2001) 3
Ticker (2001) 2
‘Manos’ the Hands of Fate (1966) 1
Baby Geniuses (1999) 1
Object of My Affection, The (1998) 1