#1: Omega Speedmaster Professional Cal 321 Vintage 1967, Manly, badass, moonwatch, with timeless style.
#2 Rolex Submariner 1680/8 18k blue dial, Cool beyond belief, gold, badass, with Gold Coast street cred, colour change dials are even better. Worn by Lloyd Bridges, not rappers.
#3 Rolex Milgauss GV, modern, high tech, beautiful
#4 Rolex Daytona Zenith Movement 16520 Vintage 1987 (birth year) Porcelain dial on brushed bracelet, the ultimate SS modern Daytona, the most beautiful dial Rolex has ever made for the Daytona, and the rarest of all Daytona with under 400 produced, even more unique than the Paul Newman
#5 Patek Phillip 5970P, Its hard not to aspire to a Patek chronograph, and this one would be my favorite. This is also the model stolen by a hooker in a hotel room from Charlie Sheen.