I don't get why this is funny. could someone explain?

I think it's a biting satire on the state of affairs over in the country we've occupied by force (for no real reason) and will "democratize" from this point on. A McDonalds here, a Starbucks there, hey, even a Supercuts.
The first haircut of course, is the one given to the ousted leader of the country that was just "too dangerous to leave be."
Now there is freedom there, and within that freedom is the choice of hairstyles that were never allowed under that brutal regime.