I use “history” loosely since G-Shock, Casio F91W come to mind and I don’t think those have as rich a history as some Swiss watches do
If you include homage watches the SteelDive sd1970 captain Willard or the cadisen 62MAS homage or a merkur w10 field watch or a type A or B flieger (like the one from escapement time). You can also ask in r/Chinesewatches to see what other examples they come up with.
The Casio mq24 was worn by the Pope and steeve jobs I think.
Any seiko 5 if you take it as a representative of the whole history of the seiko 5 family but these days it’s hard to find one new for under $100.
You can also make yourself an homage to a skx or a 62MAS or a slim turtle or some other watch (usually seiko) you find to be historicaly significant from parts from aliexpress. You can find inspiration on the r/seikomods.
Vostok Amphibia. Russian with a watch unique case/gasket construction. Dates back to the 60s and there are hundreds of different designs, the most popular being the scuba dude.
In a movie, too!
Citizen Promasters you might be able to grab for that price have some history with the Marina militare
f91w was used in terrorism
Most infamous watch in the world, worn by a president of the United States and hipsters, to Osama Bin Laden and AQ/ISIS.
Shanghai 8120: Has China’s Standard Movement which was the basis of chinese watchmaking, and Shanghais are highly collected by Chinese watch guys in general
Lorus rm349jx9: Civilian version of a long-time RAF issued quartz chronograph. The original was a Pulsar, a sister brand of Lorus
Vostok Amphibia: Mentioned in another post