Portrait of Ruin was the very first handheld CV to actually FREEZE on me.
It was a stupid glitch, too. I can't remember exactly how I did it, but it had to do with turning into Charlotte's owl form, thenn switching to Jonathan. When I accidentally went offscreen without her, she tried to teleport back to me in owl form. But it didn't work, since she was FLYING -- she never hit the ground and just kept telporting and falling in a spot in the air.
After about a half minute of this, there was just too much loading and unloading of her owl sprite for the DS to handle, and...
CRAAAAASH!
(THis was in the rainy forest stage, of the 4 last portraits)
I was pissed cuz I hadn't saved for about an hour (dumb, I know). I'm even more pissed that glitch is probably fairly easy to replicate on accident again. As a result, I'm very cautious about using Charlotte as an owl.