The boss is a large, intimidating man, who preys on the weak and small like our main character. As the main character is the smallest of the workers, he's the prime target. This boss character needs to be wide, muscular and almost engulf the screen any shot he's in. Here is a variation of hairstyles I tried out:
When I tired to create the side view of the face I realized I needed to make the head more egg-shaped to add more weight to the chin. With this new addition drawn on I made a more refined design:
An attempt at the boss's whole body, though I think it needs to be more tall and less stubby:
Here's some attempts art some face expressions:
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