Quote:I know I could search for previous threads about collisions, but I just prefer to start a new topic.

So, you're lazy. I'm bored. I'll take pity on you for now...

Collisions between moving objects.
Simple physics needed!!!
Maths and Physics Forum

For a realtime simulation you will need to use code to calculate collisions (and responses), but if you're just looking at making a rolling demo with no interactivity then you can probably get a 3DSMax plugin (or built in feature) to calculate the physics for you and export as a suitable animation/path.

Jack