With #24, I took out the background and in the second image attempted to add color to the face. Unfortunately, I hadn't bothered saving my layers last night so it's not my best work. The third image is the original. Good luck and hope your boss gets a kick out of it!
I've thought about it a bit and although I'm currently juggling a bunch of projects right now, I think I'll be able to rosy up your bosses complexion a bit (still with the oil painting aesthetic as I don't have time to redo it) as well as make it a cut-out by night's end. Granted he'll still have a smirk as I unfortunately used the wrong photo, but it should be most of what you want :-)