For each Clipping Path (upper/lower hand) you need to have a separate object below, selected together with the Clipping Path; and the upper hand needs to be a Compound Path (to form one path).
If I understand you right:
Thank you, got there in the end!
Glad we could help you.
Can you show us your final result please?
Based on Help.png (and Help2.png), I had the (mis)understanding that you wished to have:
1) Different parts of the background image showing through the two hand shapes with a certain contrast, (the bottom dark part showing through the upper hand) to form a cumstomized I,
2) Leaving the letters M CA and THEATRE black,
3) Maybe some incorporation of the grey swirlies.
1) would require the upper hand as a Compound Path, and two instances of the background image, one for the Clipping Mask of each hand, and each instance moved to fit into its hand with the right colouring; this can be done after creating each mask and Direct Selecting the image instance.
3) would depend on the way of incorporating the swirlies. If they are to appear as part of the background in the mask(s), they must be included with the colouring, maybe by Grouping them.
From your answer to pixxxelschubser, I believe he has it right, that you wish to have just one Clipping Mask with all the letters/hand parts, which must then form one Compound Path.
I too hope you will share the final outcome.