The Harley-Davidson Sportster arrived in 1957 with its now traditional 883cc motor, only at the time it was the Shovelhead engine. The Shovelhead had the same displacement as the Flathead engine in use on the KHK model, but the Shovelhead utilized overhead valves and, along with its bigger bore and shorter stroke, gave the Harley-Davidson Sportster more horsepower. Like the Silent Grey Fellow model from earlier in the century, the name, Sportster, was cast into the gear case cover. For the next 50-plus years the Harley-Davidson Sportster would undergo changes and upgrades, but Harley’s model line-up would never once omit the Sportster model.

For 1958 H-D launched four Sportster models: XL, XLH, XLC and XLCH. The H stood for high-compression while the C denoted competition. Both the XLC and XLCH were off-road models stripped of all street-legal requirements (but made street-legal the next year). In 1972, the Harley-Davidson Sportster would receive a bump in engine displacement to 1000cc. Up until 1975, Harley-Davidson Sportster models came with a four-speed gearbox shifted with the right foot. For that year the Department of Transportation mandated that all motorcycles come standardized with a left-foot shifter.

In 1977 Harley-Davidson launched the sportbike-themed XLCR (café racer). The XLCR featured a modified frame with longer frame rails to reposition the rear shocks for better handling, while its bikini fairing, gas tank and tail section were constructed of fiberglass. Traditional Harley riders didn’t understand it, and it sold poorly.

In 1978 Harley-Davidson celebrated its 75th anniversary, and the Sportster Anniversary edition featured midnight black paint, gold trim and limited-edition graphics. The year 1979 marked the last year of the XLCH and the introduction of the XLS, which is the Harley-Davidson Sportster version of the FXS Low Rider and featured a siamese exhaust system.

For 1986 the Harley-Davidson Sportster received Harley’s new Evolution engine in both 883cc and 1100cc sizes, with the 1100 being bumped to 1200cc in ’88. In 1991 the four-speed transmission gave way to a five-speed gearbox, and by ’92 all Harley-Davidson Sportsters were using a belt final-drive instead of chain.

In 2004, the Harley-Davidson Sportster got a stronger but heavier new frame that placed the engine in rubber mounts to suppress the earlier model’s omnipresent vibration. Fuel injection replaced carburetion in 2007. In 2009 Harley-Davidson launched the dirt-track-inspired Harley-Davidson XR1200 Sportster, and in 2010 the American Motorcycle Association introduced a spec racing series for modified Harley-Davidson XR1200s.