If you want to get a photo edited by Fridman (and he's still there on Twitter, taking requests, so you can), the best way to go about it is to ask him to do something. That's part of the fun, and that's where most of the humor comes from. If you just tell him to do anything he pleases, it's less fun for him. It also suggests you have a lack of imagination. Don't do it!
He made an exception for this guy, though, and that's probably because of all his elaborate headgear. This, very clearly, is a man who likes to party. Fridman was so impressed with his commitment to partying that he decided to put him forward as a candidate for the Presidency of the United States of America. Given this third-way option, we wonder if the end result would have looked any different?