Stepping out of a TV - HELP - Moving between 3D layers in Shake

Hi,
So I have a concept that involves a chroma keyed person 'stepping out' from a TV.
Not sure how to move a character leg by leg from behind the frame/border of the TV (ie. the 'screen') to in front of it, onto the table.
Would I need to rotoshape around each leg frame by frame to 'bring' them into the foreground as he steps?

Perhaps this is bizarre, or perhaps it's a technique everyone's had a stab at at some point. Either way, I've no idea where to start and would be greatly appreciative of any advice.

Thanks in advance!
🙂