Tricky Lighting Question

[Gohanto]

For a shot I need, I need to have a character well lit for most of a conversation, but then put a baseball hat on to drop his faces completely into shadow. The hard part is, if I lit stongly from above for the first part of the shot, the shadow looks fine, but it's looks strange before he puts the hat on (part because his eyes are deep-set). Or if I use fill lighting, his face doesn't get dark enough.

Any advice?

 

[Cool Lights]

Can you try some trick where you dim the fill lighting suddenly as he puts his hat on? That's the only thing that comes up for me at this point.

 

[cardmaverick]

What are you using for post? You could do some power masking tricks to help you out

 

[Allen Green]

I've used a camera light (eye light) Frizzi (dimmable) to pump a little light on the face under the cap in addition to the key light.
Good luck
A.G.