Time was, you'd Google the phrase "entry-level Harley" and the results would be page after page of articles about the Sportster. Let's be honest, the Sportster is far from a beginner bike. Yes, it's relatively light and maneuverable (for a Hog), but there's a reason that it was favored by Sonny Barger and is beloved by Sportster owners everywhere—the 883cc engine gives the Sportster some kick, perhaps a bit more power than many new riders can handle.
New riders who have their hearts set on buying a Harley would be better off picking up either a new Street 500. Aimed at new riders as well as riders who are looking to make the leap to a Harley, the Street models offer a lighter, city-friendly cruiser with open-road capability. There have been concerns about build quality, and the 500 might be best suited for instructional courses, but if you're looking to join the Harley crowd the Street might be your ticket.