The first Sportsters were introduced in 1957. By 1999 the Sportster name was still very much in evidence, the lineup consisting of the Sportster 883, Sportster 883 Hugger, Sportster 1200, Sportster 1200 Sport, Sportster 1200 Custom and the new Sportster 883 Custom. The Sportster models have had the longest production run of any Harley-Davidson motorcycle. Perhaps this can be attributed to the Sportsters racing heritage or its affordable price. Or perhaps it is because Sportsters provide a torquey, about-town ride. But one thing is for certain: Sportsters have always held their own, pumping Harley-Davidson authenticity through every valve, cylinder and exhaust note to the delight of all Sportster enthusiasts and riders.

Additions to the Sportster family are always welcome and for the 1999 season along came the XL883C Sportster 883 Custom. The look of its custom styling features, the sound of its 883cc-powered Harley-Davidson engine, and the feel of its longer front end and forward controls create a great motorcycle for tremendous value. Great news for all those riders who want to join in the Harley-Davidson experience and who want to be part of the Sportster scene. Borrowing styling cues from its Sportster 1200 Custom cousin, the Sportster 883 Custom boasts longer front forks and forward foot controls which not only look great and enhance riding comfort, but also give the bike a more radical riding profile. New sleek drag bars, a chrome bullet headlight incorporating a quartz halogen 55-watt low beam and 60-watt high beam, and a sporty two-up seat add to its stylish custom flair and give the bike a little street-racerstyle. The turn signal lights are self-canceling, the seat height of the bike is a comfortable 27.56 inches (70.0cm) and the Ground Clearance is 6.7 inches (17.02cm). The rear suspension, which is a recalibrated version of the XL883 Hugger rear suspension, supports two-up riding comfortably. The Sportster 883 Custom features a solid disc 16-inch (40.6cm) rear wheel and a laced 21-inch (53.3cm) front wheel. Finishing touches include a chrome speedometer.

On all Sportster models, a new sealed tail light unit helps to prevent internal condensation and possible malfunction, and there is an accessory-ready hookup. Where once there was hard wiring, this is now replaced by a circuit board, making tail light servicing easier. These overall design changes further enhance the bike's durability. The small tank's 3.3gal (12.5lit) maximum fill-up could be a little limiting especially on a long run, even though the miles per gallon return is an average 53mpg (83kpg).