I'm not sure if anyone is still following this thread or cares, but I've always found this video to be quite interested. Consensus boils down to creative cutting/styling and hair fibers. He just has a tendency to occasionally overdo it on the fibers, so you get situations in which he'll be rocking a buzz cut, end up using too much concealer, and then his hair just looks painted on at that point. However, at the end of the day, he's still a hair icon and was a massive inspiration for the undercut boom I recall seeing hit NYC a number of years ago.