here’s a quick and dirty way to do this…results may vary.
build your animation and place in the timeline where you need it (layer1). Now, at the point when the object is going to pass through the talking head(layer2), razor and move the remainder to layer 3. Go back to layer one and extend the tail a few frames…the animation will be exactly what you had placed on layer 3….extend these tails to the point of when the logo/text/etc. would be all the way through the head. The reason to do this is to sell the ‘passthru’….since probably not all of the logo/text/etc. will pass thru the head at once, it will look like there’s still some of the logo behind the head, and some in front.
Go back to layer 3 and add an edge feather or something along those lines to clean up the effect.