Best Movement: Grand Seiko Spring Drive
Most Interesting: NOMOS Weltzeit
Best History: Cartier Tank/JLC Reverso
If you’re dying for a Rolex: Air King 1500
Cool Military Watch: Panerai Due 38mm
Many other considerations out there, I would also add look at Tudor, preowned IWC Portuguese, and the Omega Seamaster 300. The Omega Speedmaster is also a classic.
Cartier is the most versatile in my opinion. You can dress it up to a tuxedo or down to sweats at home.