Haven't worn a watch for 20 years. But if I was a multi-millionaire, I'd buy a George Daniels or RW Smith watch, just for the badassery of having something so incredibly intricate that's totally hand-made. He makes 10-12 a year, they take at least 2 years to make, all the parts are made from scratch in his workshop. They start from about $150,000 each.
My grandma brought me a watch from Japan one time that had a game in it. You had left, right, and center buttons. Center would make you jump or throw ninja stars, depending on where you were at. It was some bad ass lil ninja game on it. So ill. It was Armani.