I have seen people bash IDA into something quite nice here although it is nowhere close to what you describe. Emulators often have something half nice here (a very basic variation would probably be GBA and DS emulators where they will allow you to know what mode you are running in at a given point in time and going further some of the stack/"register"/flag/matrix viewers). Hex editors with memory viewing options are quite nice as well and I saw a presentation a while back where some people did colour mapping to it and figured out where maps, fog of war and such like were to make cheats.
I suspect what you asked for will be held up by the halting problem or some minor variation upon that. Branch prediction and read ahead or Just In Time compilers/stepping though might get you somewhere, but it would be very involved and if calculated pointers, proper memory management and whatever else get involved for more than a handful of occasions then I would give up there and then.