I was thinking about using pudding as a filling with crushed oreos cookies (the kind with chocolate filling) as a filling for a cake. Does that sound good or am I asking for trouble?

The cookies might get really soggy. I would probably put them in a buttercream instead, but maybe someone else has already tried this and can give you better info?

The cookies will get really soggy. Think banana pudding with nilla wafer cookies--just nice a soft for a day and after that it's mush. And since the oreos would be in much smaller pieces, I think it would be mush much sooner. Still, it does sound good enough just to experiment with, I can see why you would consider giving it a shot.