
1957 XL Sportster
It was the mid-1950s and Harley-Davidson needed a motorcycle to compete with the lighter, faster and bigger displacement competition coming out of Britain. For the 1957 model year, it took its relatively successful K Model (which first appeared five years earlier in 1952), increased the displacement from 737cc to 883cc, replaced the side valves with more efficient overhead affairs and swapped the finned aluminium cylinder heads to iron ones, which earned it the Ironhead designation. Its success was such that by 1958 the Sportster had spawned another high-compression model, the XLCH, and the rest, as they say, is history. The legend of the XL 883 Sportster was born.

1977 XLT Touring Sportster
The 1977 Touring model stands out as one of the most significant departures from the original Sportster theme and, as a result, one of the shortest lived, too. Twenty years after the nameplate appeared, and now under AMF ownership, the 1000cc Sportster hit the market complete with a windshield and panniers and was met with wildly mixed reactions. But ultimately the purists won and the Touring Sportster was discontinued a short time later. The 1977 model year is also significant as being the year a disc rear brake was introduced across the stable, replacing the drum set-up. Speaking of brakes, the firm’s first-ever twin disc front end appeared on the iconic but short-lived XLCR Cafe Racer.

1977 XLCR Cafe Racer
Quite possibly my favourite Harley-branded motorcycle ever, the XLCR Cafe racer stands out for two significant reasons. Firstly, it was quite a clear deviation from anything we’d seen out of the Milwaukee factory in the two decades since the Sportster’s introduction, and secondly, it proved Harley-Davidson could swing its focus to where demand was and respond both quickly and effectively to market trends. Penned by the firm’s Willie G. Davidson, it was a boldly all-black cafe racer-styled Sportster. Despite its charm, the H-D purists couldn’t fall for it and to the cafe racer racer set it was still a Harley-Davidson and as a result, unfortunately only remained in production for one more year.

1991 XLH Sportster
The first production run of the 1990s wasn’t particularly memorable, except for the fact that the 1991 model year was the introduction of a five-speed transmission to both the 883cc variants and the 1200cc, which was introduced three years prior in 1988. Before then, all Sportster models employed a four-speed ’box but, back under the Davidson family ownership (which occurred in 1980), much-needed updates began to appear. Belt drive debuted across all of the 1200cc models in 1991 before the entire Sportster stable switched from a chain to belt drive by 1993. A notable occurrence in this era, also, was the lighter and more reliable Evolution motor that replaced the Ironhead stalwart five years earlier in 1986.

2008 XR1200
Although the first 1200cc Sportster appeared some 20 years earlier in the form of the 1988 XL1200 Sportster, the 2008 XR1200 was something else. Harking back to the firm’s wildly popular XR750 and its stellar race record, and reminiscent of the firm’s 2001 883R which represented a leap forward in handling and braking, Harley-Davidson tugged on the heart strings of fans and introduced the big-bore flat tracker for the road. It first broke cover two years earlier at the Intermot Show in Cologne, Germany, and attracted much attention and fanfare. It was the American firm’s first sportsbike and on its release, spawned a one-make race series in the States. Despite its promise, the purists would once again prevail and the XR1200 was discontinued by the 2013 model year.

2011 XL1200X Forty-Eight
The Forty-Eight stands out as the time Harley-Davidson paid homage to the very beginnings of the Sportster 50-something years after the nameplate made its debut. Nine years earlier, in 1948, the firm’s 125cc Model S was the first machine to use the so-called peanut tank, a design that would eventually become a signature of the Sportster line-up. Ironically, the bike’s stand-out feature would also become its stand-out flaw, for to achieve a realistic and attractive peanut-shaped tank that was well integrated into the motorcycle’s design, the 1200cc motorcycle fuel capacity was reduced to just eight litres. Elsewhere, it was the pinnacle of cool, however, with its fat front tyre, wire wheels, single seat and chopped fenders.
