Top Of Mind: Omega Speedmaster Moon and Rolex GMT.
Speedmaster Moon for obvious reasons. Rolex GMT also because many astronauts were former pilots and ergo owned such a watch prior to becoming astronauts. But the Rolex GMT was also a popular watch among soldiers in the Vietnam war and therefor a watch with a lot of history.
Today, however, every single brand is eagerly trying to buy into some sort of unique history. But the two aforementionend watches truely has history, helped without advertising, but sheer need.
Tool watches at its best!