Ah, the legendary Sportster. A motorcycle that has changed so much, but also so little, since it’s introduction in 1957. Let’s get this out of the way, though: my opinion here applies to the sweet spot of 5-speed, frame-mounted Evo Sportster models, meaning ones made from 1991-2003. Everything after that isn’t as hot. Rubber-mounting the engine to isolate vibrations for a “smoother” ride (yeah, not so much) took a 500’ish pound motorcycle and turned it into a 600’ish pound motorcycle. Where elsewhere, motorcycles were being engineered to be increasingly lightweight and powerful, the Sportster has only gotten heavier and less punchy, which is decidedly antithetical to the notion of being “sporty.”
Those 12 years of relative perfection, however, are pretty great. It’s a visceral experience riding these older Sportsters. It’s like a hot-rodded riding mower. It shakes and it vibrates and simultaneously feels like it’s solid, durable, and planted while on the verge of exploding apart all at the same time. Handling presents a similar dichotomy between being slow and heavy and nimble. At low speeds, it’s like trying to wrestle a walrus. Get it moving, and it almost (almost?) feels as agile as a UJM from the 70’s. Suspension is inadequate in its stock form, and must be upgraded if you want to ride it hard and make the most of the Sportster’s capable engine. Objectively, it’s not a particularly good ride, but it has so much character, tries so hard to actually be a good motorcycle, and is so at odds with itself, that it transcends objectivity.
It’s also a ruggedly-built bike that is easy to work on, thanks to everything being held together by easily accessible fist-sized bolts. This is a huge advantage, since you will be wrenching on it often, both in regards to maintenance and repairs, as well as customizations. Despite having only owned mine for a short five months before it got totaled in a wreck, I spent more time working on it than any other bike I’ve owned, especially in relation to the time owned. Some of that was the need for constant maintenance, adjustments, chasing down gremlins, and putting Loctite on stuff that had rattled loose, but a lot was done in the name of customization. That predilection for customization is what makes the Sportster a truly special motorcycle. It’ll also score you major cool points, because HARLEY, but not too many cool points because “IT’S A GIRLS BIKE!”
As a cool motorcycle that is a versatile blank slate for customization that the aftermarket has embraced like no other motorcycle ever built, these older Sportsters can’t be beat. As an actual rideable motorcycle, it’s fairly sub-par without some upgrades, so it’s kind of circular in that regard. Make it your own, and it’ll be one of your favorite bikes ever.