Back when my group was playing 3.5 we were exploring some underground ruins and we got in an encounter with a group of beasts (its been about 3 years so I can't remember which exactly they were) and we happened to be adjacent to a incredibly large hole, long story short the fight was going very poorly for my party and the monk decided to grapple with one of the creatures and then dragged it and himself off the edge of the cliff.
Somehow he was able to break the grapple, brace himself against the sides of the pit, stop his fall and climb back up. By the time he made it to the top the tides of the battle had changed yet he decided he was invincible and decided to attempt this again.
This time he was unable to break the grapple in time. KA-Splat. Our DM was kind enough to allow us to climb down and find enough of his body to resurrect.
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