So we started taking him to a nearby salon that specialized in kids haircuts. He was coddled with TV, video games, toys, chairs that look like racecars, etc. He still screamed and squirmed but at least he was in the capable hands of stylists that were used to cutting kids hair under these conditions. It was pricey, but I considered it to be worthwhile because I could step out of the role of Terrible Mommy with the Scissors/Clippers. Eventually, he stopped being so upset at haircuts, even looking forward to the balloon he would get at the end, he would even let them use the clippers! Once we got to a time when there were no more tears, we decided to start taking him somewhere less expensive. And then I got to thinking, I have these fantastic clippers at home, and could really just skip the driving/waiting/paying bit, and just do this myself. So, the other day, I popped A Bug's Life into the DVD player, rolled up the livingroom rug, and put my son on a chair in the middle of the room. He was OK with this, as I told him I'd pay him some money for his piggy bank (as I'd be saving $12 on a haircut elsewhere). All through the haircut he kept cringing, whining and complaining about the clippers "hurting". I thought this was ridiculous, after all, they are just clippers! No sharp blades risking contact with skin, plastic guides in place to make sure I didn't cut anything too short, everything was as it should be. So we (he) powered through.