8. FLSTF Fat Boy

Year: 1990
Complex Says: The Fat Boy took a little bit of this from the Heritage Softail Classic and a little bit of that from the Softail Custom, then recombined it to make something dramatically different, stylistically speaking, than anything Harley had previously offered. Solid disc wheels. Flared fenders. A 1950s bomber look, straight from the factory. It was a bit like the Jetsons version of a Harley, only way cooler than that sounds. More importantly, people bought it en masse.