For me:
Conker's Bad Fur Day :D
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Mortal Kombat on the Genesis. I don't think there was an ESRB back then so it wasn't technically "M", but it did have a 17+ sticker on it.
Probably Mortal Combat when I was a kid. Used to have nightmares of the levels where you could kick a guy in front a train or into a pool of acid and see his bones afloat. ;)
It wasn't rated M, but Zombies Ate My Neighbors gave me nightmares more than any other game I've ever played; so it kind of worked as if it were my first M :P
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