When you're doing caricatures, bear in mind that there are other elements to an image than a big head and details in the body. If, for example you are doing a guy who prides himself in the fitness and strength of his body's muscle bulk and definition, whether or not it shows to the casual eye, you may want to consider exaggerating the size of his brawn. Right now, with the scale of the head, his body looks a little physically weaker than you want to, which I doubt you're after as a look.
The other thing I can tell about this fellow from his photo is that he is somewhat flashy. That means you can also exaggerate those things like his jewelry, his chains, his sun glasses, and if he had a car, you would want to make that look as hot as possible.
I don't know if the girl is safe to remain in his life or not, but I kind of get that her beauty and sexiness is something he also "wears".
So I could see you doing a great caricature of his head, as you do so well, but make his body really huge in the shoulders, chest and biceps. You could have the girl clinging to him like in a Frazetta painting or one by Boris.
Looking at him, the contemporary celebrities who I immediately think of are Vladimir Putin and actor Vin Diesel. Very masculine. Fast, hot shots, and with all the alpha male trimmings.
So sometimes you may want to push things further. However, if you're afraid you might offend (which is always a risk), you can play it safe and merely exaggerate the things you are doing and avoid the psychological portrait.
Anyway, those are some of the things that you could push if you ever wanted to take it to the next level.
The recognition quality of the head is fantastic as ever. You are very good at that stuff.