Few brand names are as closely associated to the cruiser style as Harley-Davidson. The Milwaukee-based company has a long history of making iconic cruisers and it hardly gets more iconic than the Sportster, a name brought to life in the late 50s.
Today’s modern Superlow iteration of the Sportster is an door into the H-D family. While the brand has a bt of a rep for being overpriced, the Superlow gets you on a H-D for less than $9,000. Granted, it isn’t powered by the company’s famous big-bore Milwaukee-Eight 107, but its 883cc Evolution is a good entry-level mill to get a taste of what makes Harleys so fascinating. It provides a more upright riding position—the handlebar and footpegs aren’t as front-set as on other cruisers on this list—and it tips the scale at only 569 lb, making it a great place to start in the realm of cruisers.
Pros: iconic, lightweight, easy to get on
Cons: older technology