History of the Harley-Davidson Sportster : The Harley Davidson Sportster had been produced since the late 1950s but its roots date back as early as 1919 with the iconic Model W motorcycle which featured a unique flat-twin engine. The Sportster has seen many changes over the years but one thing has always stayed the same: the die-hard fanbase behind them. Whether someone is just getting into motorcycling or has been riding motorcycles for decades, the H-D Sportster has all the power and attitude.