We played through the AD&D Tomb of Horrors 3.5 version with some Pathfinder characters. It did not go super well. Originally it was supposed to be seven players entering the Tomb. By the week of the event, two guys bailed due to work, and a third had to cancel last minute, and a fourth had to go about two hours in.
They explored one room, two frescoes, and a hallway full of pit traps in that time. There was a gargoyle in there as well, it dealt like 169 damage to Jeremy's Rogue over the course of two rounds. He died. Lance and John very creatively defeated the mutant gargoyle, with a combination of a second level laughing spell and a storm of lightning bolts. Everyone seemed to enjoy the savagely difficult fight, but walking around gave them a kind of analysis paralysis where I told them their surroundings and said, "What do you do?" and they stared blankly at me, terrified that touching a door would unleash death. Which did not stop Jeremy from just yanking on a lever he found in a trapped chest built into a fresco. Luckily, his Reflex save was good enough to leap away from the pit trap he opened under his feet.
They ran into some trouble when they encountered a magical arrow trap that fired arrows every round and Eric the Monk and Jeremy the Rogue decided that there was no way they could deal with it other than to do nothing on their turns. They figured out that it was a magical trap though and everything ended up being alright.
No one really communicated with each other at all as to what they were going to be, so John ended up making a Druid with no real healing abilities and Lance came as a Sorcerer and not a Cleric like he had said, so the group had no healing and they had to rest outside of the Tomb after the fight with the gargoyle. Lance was pretty useful, but I think overall that the Tomb would be easier if they had a Wizard, that class has so much utility for a place like the Tomb. I mean, a Sorcerer works fine, but a utility Sorcerer just doesn't have the same feel as a lightning bolt flinging fireball dropping draconic bloodline sorcerer.
Also, evidently Sorcerer bloodlines are too complex a concept for Mr. Butch-Ass-College-Educated-Worked-For-Boeing-Engineer-That-Doesn't-Own-Graph-Paper-Or-A-Ruler. You know who you are, bitch. Hehe.
Overall, it could have gone better, but things come up and shit happens and the majority of the group seems to be interested in wandering back in to see if they can conquer the evil of the Tomb. Hopefully we end up being able to schedule it again, I'd really like to see how they deal with some of the more interesting and tricksy traps in the place.