Even with all its flaws, I love running people through Tomb of Horrors.

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2 points

With a GM? Jailbreak for Unknown Armies, hands down. Needs to have 5, best 9 people for the best experience. There is a newly released freely downloadable version made converted to another system on DTRPG afaik. GMless? Probably Alice is Missing, though I really like 10 Days Without Sunlight (as long as the scoring mechanic is ignored).

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