Building a New List of Top 250 Movies

I’ve officially caught up on watching movies for Blank Check with Griffin and David. Huge accomplishment. This dates back to 2023, when I made a concerted effort to expand my base of film knowledge. The projects included not just Blank Check but also Unspooled and the Criterion Challenge1. I’ve watched maybe a thousand new-to-me films, covering random classics, little-known charmers, full director filmographies, and outright dogshit.

Part of the inspiration was the year 2022, a banner year for cinema, when I saw a lot of great stuff in theaters. In the middle of that year, about six months before all this began, my group of friends and I made lists of our top 100 movies and then compared notes. It took over a week to remember all the films2 and my final version was somewhere between “a lot of this feels right” and “man I should watch some more films”. It had recency bias and I’m sure I forgot a bunch of things I’d seen.

I’ve always quite liked the list, but it’s always felt incomplete. There are certain movies on there that are great but probably only made it in because I remembered to include them in the ranking engine3. The remedy? This massive knowledge base I’ve built up over the last three years needs to go somewhere.

So it’s time to build a new list.

Building the pool…

Given the sheer volume of films that I’ve crossed off the list in the last three years, a top 100 feels like it won’t capture the full breadth of what I’ve watched. As such, the list is going to be a Top 250. Any bigger than that and the list will get unwieldy approaching a survey of “movies I’ve watched”, rather than some powerful ranking. If the tail end of the list (or any of it, really) has a number of films in the “yeah, I guess?” category, then this will be a failure. The goal is to come up with a list so good that there’s a robust number of films that don’t make the cut. Ideally, their omissions will amount to sacrelige.

All of the films I’m grabbing are going to come through Letterboxd. Early in my Letterboxd user journey I went and rated as many films as I could think of, going back year by year. If I’d seen it, I marked it. As of this writing, there are about 800 films on Letterboxd to which I’ve given at least four stars. I’ve not reviewed all of these. I’m sure a lot of them are guesses (and some movies rated unfairly low), but going through and marking/saving movies is an imperfect science. I’m good with this rating system as a barometer4.

There is, however, another issue. Which leads to…

A new series!

I’ve done over a thousand reviews on Letterboxd since becoming an active user, but there are a ton of films that fit into the category of “only seen once”, “haven’t seen it in a long time”, “would like to revisit”, or some combination of the three. There’s a lot a lot of these (especially “would like to revisit”), but there’s only so much time to get all this done.

With 27 weeks left in the year, I looked at the movies in that 4/4.5/5-star range and selected about 40 films that I really do need to watch again. I was pretty ruthless, cutting that pull to 25 films that I’d like to write about. There’s a bunch not on here that I’d be rewatching otherwise (like a full Coen Bros rewatch for Blank Check’s forthcoming miniseries or finishing out remaining Paul Thomas Andersons before One Battle After Another or a Tarantino rewatch just because), but what’s left is an eclectic smattering of movies that perfectly fit into these categories.

If nothing else, it’ll be a good excuse to talk about these films. This is a great opportunity to share previous feelings, unpack how that’s changed in the afterglow of fresh eyes, the new odds of it making the list, and/or how high I think it might go. They’re all great films that (with one exception) I wholeheartedly recommend.

These reviews for these will run on Fridays for paid subscribers and will culminate in a daily reveal of the list at the end of the year.

Without further ado, here’s the list/schedule so you can watch along at home!

1. Before Sunrise - July 4th
2. Eternal Sunshine of the Spotless Mind - July 11th
3. Cloud Atlas - July 18th
4. Bridge of Spies - July 25th
5. Midnight Run - August 1st
6. Sunset Boulevard - August 8th
7. Serenity - August 15th
8. Dunkirk - August 22nd
9. Taxi Driver - August 29th
10. The Good, The Bad, and the Ugly - September 5th
11. Before Sunset - September 12th
12. The Royal Tenenbaums - September 19th
13. Synechdoche, New York - September 26th
14. Twelve Angry Men - October 3rd
15. The Wolf of Wall Street - October 10th
16. Seven Samurai - October 17th
17. The Treasure of the Sierra Madre - October 23rd
18. Grand Budapest Hotel - October 31st
19. Airplane! - November 7th
20. To Kill A Mockingbird - November 9th
21. Before Midnight - November 21st
22. Moonrise Kingdom - November 28th
23. Unforgiven - December 5th
24. Casablanca - December 12th
25. Vertigo - December 19th

• Top 25 Films that didn’t make the list5 (with commentary!) - December 26th

• A Daily Coutdown of My Top 250 Favorite Films of All Time™ (2025 Edition) (with commentary!) - December 27th-31st

This should be a blast. Thanks in advance for joining.

Now let’s go watch some great movies.