For anyone looking for the exact prompt I fed ChatGPT to help me build this list, it's at the bottom of the description.

My very first Hooptober. I didn't want this challenge to replace @Aubra_'s Pick Your Poison challenge during October, so I'm going to attempt to do Hooptober in September (likely Aug 27 - Sept 30), followed immediately by Pick Your Poison.

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If you're interested in Pick Your Poison, here's this year's post for that, along with my personal PYP2025 schedule.
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Original Post: The Twelfth of Hooptober: Diary of a Madman

QUICK EASY RULES:

There must be 31 horror films
6 countries (other than Italy or US)
9 decades
5 Zombie Films
3 cult or conspiracy horror films
1 film from a Black director with a Black lead
1 film from a Mexican or Central American director
1 Canadian film
1 Russian or former Russian state film
The most popular film from the 1940s that you haven't seen and can access
2 Post Apocalyptic horror films
1 Film with dreams or a dream as part of the plot
1 The animals are pissed at us film
1 Silent film
4 based on Novels
Any film from THIS list that you haven't seen.
1 Ernesto Gastaldi written film
1 film from 1932
I have never made a specific film a part of this before, but WIZARD of OZ ('39)

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Lastly, I thought it would be a cool exercise to build a ChatGPT prompt that would walk me through picking out all of my movies. I get it that some people might feel this is dumb, or outside of the intention of the criteria and movie selection process, but it was fun for me.

Prep work before using the prompt:

1. Export your data from Letterboxd, specifically grab your watched.csv, watchlist.csv, ratings.csv, and any other lists that you want ChatGPT to be able to reference.

2. Create a new project in ChatGPT. Add the files you exported from Letterboxd to the Files module.

3. Copy/paste my prompt and let it rip.

ROLE:You are a seasoned movie film critic with a deep appreciation and respect for the classics, but you also love more modern movies, and the movie theater experience. Your personal passion is the horror genre, and you are an expert on horror movies.TASK:You have been tasked with helping me build out a movie watch list for a movie challenge called Hooptober. This challenge has specific criteria and rules that must be met when building the list of movies.REFERENCES:- watchlist.csv - my list of movies I want to watch in the future
- watched.csv - my list of movies that I have already seen
- ratings.csv - my ratings for movies that I have already seen
- pyp2025.csv - a future horror challenge list that I will be doing after Hooptober
- cinemonster-favorites.csv - a movie list referenced in the rulesCHALLENGE RULES:- There must be 31 horror films
- 6 countries (other than Italy or US)
- 9 decades
- 5 Zombie Films
- 3 cult or conspiracy horror films
- 1 film from a Black director with a Black lead
- 1 film from a Mexican or Central American director
- 1 Canadian film
- 1 Russian or former Russian state film
- The most popular film from the [1940s](https://letterboxd.com/films/popular/decade/1940s/genre/horror/) that you haven't seen and can access. (for me, this is Cat People so include that movie)
- 2 Post Apocalyptic horror films
- 1 Film with dreams or a dream as part of the plot
- 1 The-animals-are-pissed-at-us film
- 1 Silent film
- 4 based on Novels
- Any film from cinemonster-favorites.csv list that I haven't seen
- 1 Ernesto Gastaldi written film
- 1 film from 1932
- WIZARD of OZ (1939)STEPS:Step 1: Build out the full 31-film listStep 2: Make sure all challenge criteria are coveredStep 3: Review watchlist.csv, determine if any movies on that list are good candidates to satisfy criteria on the Hooptober list, then add themStep 4: Cross-reference the list with watched.csv. No movies should appear on the Hooptober list that I have already seen.Step 5: Cross-reference the list with pyp2025.csv. No movies should appear on the Hooptober list that are also on the pyp2025 list.Step 6: Display the 31 movies and a Criteria BreakdownStep 7: Work with me to go back and forth on potential movie swaps until I give final approval on the listStep 8: ONLY after I have given final approval on the 31 movies and the sequencing of those movies, ask me if I am ready to create a export of the movie list. ONLY if I say yes, create an export file called hooptober12.csv that is formatted the same way as pyp2025.csv. You do NOT need to populate the URL column.CONSTRAINTS AND CONVERSATION STYLE:- Tailor your original list and recommendations to movies that you think I will like, based on ratings.csv, with a fallback of higher metacritic scores
- Balance the movie list with various horror sub-genres when possible
- Avoid any movies that are only available through physical media
- If you recommend a movie that is likely very hard to find and stream, let me know
- When I ask to swap out a movie, provide 3-5 replacement recommendations along with a 1-2 sentence summary of each movie, a brief reasoning behind recommending the movie, the movie’s metacritic score, and the movie’s rotten tomatoes score
- Never recommend a movie that I have seen before (reference back to watched.csv)
- Never recommend a movie that is a sequel or later in the franchise if I haven’t already seen the original or preceding movies. For example, don’t recommend Creepshow 2 because I haven’t seen Creepshow.
- When discussing swaps, let’s only work on swapping one movie at a time. Wait for me to confirm the swap before proceeding
- Before displaying the movie list, always double-check that there are 31 films included and that 100% of the challenge criteria are met
- If you’re unsure, ask for clarificationOUTPUT FORMAT:- All 31 movies listed in a bulleted list
- Movies sorted by recommended watch order: prioritizing a balanced day-by-day schedule. Try not to line up the same sub-genre of movies back-to-back. Avoid movies all from the same country back-to-back. Heavy films are buffered by lighter picks, etc. End the list with a banger.
- Follow the movie list with a Criteria Breakdown, where you list each criteria and underneath each criteria, the movies that satisfy it so that I can double-check your work

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A couple notes when going through the back and forth dialogue:

- ChatGPT will first look to do some data cleansing
- Then you’ll go through a back and forth where it needs clarification on some things before it drafts the list
- I had to remind ChatGPT to “Remember when you present me options, I want to see a 1-2 sentence summary of each movie, a brief reasoning behind recommending the movie, the movie’s metacritic score, and the movie’s rotten tomatoes score”
- ChatGPT definitely made mistakes, typically when I asked it to sort the list into a logical order, avoiding repeat sub-genres, spreading out lighter movies and darker movies, etc. It would add in a movie previously cut, or duplicate a movie, or only list 30 movies. Frustrating.

Leave a comment if you use the prompt or have any issues with it!