They're a very well known brand, put out top of the line watches which in the watch world, means quite a lot.
Watch brands try and do new stuff and many times they do hand painted dials that are unique and supposedly increase their desirability. Sometimes it works, sometimes it doesn't. I don't think it works for these, I've seen other watches that are much more memorable with hand painted dials.
Not to be mean, but the world of high end watches is beyond the income of any pool player who has ever lived based on pool income. Rare, or super limited release watches go from hundreds of thousands of dollars, to millions of dollars. The diamond additions celebrities want are another story altogether.
Google celebrity watch collection and put in John Mayer, Jay Z, Mark Wahlberg and see what real watch collections involve.