Here in Britain, we have Roger W Smith, the only watchmaker in the world who makes everything by hand. He was the principal disciple of George Daniels, a truly legendary watchmaker, who sadly died a few years ago.
Daniels famously taught himself watchmaking by taking apart old clocks, putting them back together and repairing them when he was young. If he had been born in the digital age, he'd have been a hacker comparable to Woz.
He didn't just make his own watches, he also made all the specialised tools needed. These days he is perhaps best known for the Daniels Co-Axial Escapement found in some Omega watches, which for many years was believed to be impossible to make.
If you google Roger Smith, he has lots of interesting videos on Youtube showing various parts of the watchmaking process from raw materials.
There are a few interviews with George Daniels too. Here's one talking about his first complete, from scratch watch: