The 14 Coolest Harley-Davidson Motorcycles Of All Time
Through the years, Harley-Davidson has proven itself as a thoroughly capable motorcycle manufacturer. We don’t need to tell you the effect its cruisers have had, and they’re constantly evolving, which is never a bad thing. Some Harleys make their mark by being great performance machines, some others by being great to ride, some look great, and a fair few just bring together the whole package.
Whether knowingly or not, though, Harley-Davidson also imbibed another trait into some of their motorcycles; it’s not exactly a tangible aspect, but something that you just know. Some of their motorcycles just imbibe the cool factor much better than others. And the great thing is that there’s no one era these cool bikes belong to; they’re littered across Harley-Davidson’s long existence. These, then, are our picks of some of their coolest machines.
Harley-Davidson V-Rod
Used Price Range: $4,000-$16,000
Harley was trying to evolve at the turn of the millennium, and they feared that their air-cooled V-twins might be outdated. Using the liquid-cooled eight-valve overhead cam motor from the VR1000 sports bike, the Harley-Davidson V-Rod was supposed to signal the new direction for the company.
This tubular-framed muscle bike wasn’t very well-received, though. Purists distrusted the move away from the old, reliable motors and simply couldn’t get on board. A couple of decades later, the V-Rod is still one mean-looking brute of a motorcycle ahead of its time.
Harley-Davidson FLH Electra Glide
Used Price Range: $5,000-$30,000
Born in 1965, the FLH Electra Glide is among the most iconic Harleys ever. The Electra Glide’s name comes from the fact that Harley-Davidson equipped it with an electric starter, making it one of the first bikes to have one. Along came the ‘Batwing’ fork-mounted front fairing, and with the option of hard panniers and a windshield, the Electra Glide became the first proper touring motorcycle.
Harley-Davidson FLHR Road King
Used Price Range: $7,000-$14,000
The Harley-Davidson Road King truly embodies its name to the hilt. It’s come a long way since its debut way back in 1994, but ever since then, it’s been unmissable on our roads.
It’s gone through various updates since, but the Road King’s original traits remain very much intact. It’s got a punchy, torque-laden V-twin powering it, and plenty of modern kit, too (if you pick up a new Road King, that is). For all that it stands for, this is definitely one of the coolest Harleys made.
Harley-Davidson FXR
Used Price Range: $7,500-$15,000
Many classic Harleys look great but seem as if they would struggle at the first sight of a corner. For the most part, it was an accurate assumption. That’s until the Harley-Davidson FXR came along. Engineers worked tirelessly to maintain the unique style of a Harley-Davidson while improving the handling performance.
Due to a new, stiffer frame, the FXR was much more capable in turns, and its EVO engine was a real peach. In the FXR, Harley-Davidson built a wicked motorcycle that wouldn’t be left behind on the twistier roads. And it’s becoming a collector’s motorcycle, too.
Harley-Davidson FXDR 114
Used Price Range: $9,800-$19,500
The FXDR 114 was, going by the timing of its launch, a way for Harley-Davidson to pacify the countless V-Rod fans after the latter’s discontinuation in 2017. Was it a worthy replacement, then? That’s a loaded question with no direct answer.
All that said, the FXDR 114 was thoroughly modernized in comparison. It featured a 1,868cc Milwaukee-Eight V-twin that gave a respectable amount of power. It also included improved geometry, helping it be a lot more nimble than you’d expect. The FXDR 114 was definitely a step in the right direction for the power cruiser segment on the whole.
Harley-Davidson Sportster S
Starting MSRP: $16,999
The Sportster is often the butt of many jokes inside and outside the Harley-Davidson community. The ‘baby Harley’ is too small and too slow for many. To counter this, Harley-Davidson released the Sportster S — a completely new take on the Sportster name.
With the same rowdy 1,252cc Revolution Max motor as the Pan America, the Sportster S is lightning fast. Its chunky tires and thickset looks really give it the feel of a proper muscle bike, too, perhaps meaning that the Sportster S will surely succeed where the unfortunate V-Rod failed.
Harley-Davidson Pan America
Starting MSRP: $17,699
Yet again, Harley-Davidson surprised the masses with the release of a motorcycle that falls way outside their core customer base. The Harley-Davidson Pan America is a 1,252cc adventure bike that can take you worldwide.
Producing 150 hp, the Pan America is one of the most powerful Harley-Davidsons ever. With its upright riding position, you can comfortably cover huge distances on one of the most impressive adventure bikes.
Harley-Davidson Fat Bob 114
Starting MSRP: $18,899
One look at the Harley-Davidson Fat Bob 114 and it’s unmistakable: this is one drool-worthy cruiser. Right from the beefy tires, the no-nonsense design, and the low-slung nature, the Fat Bob was destined to evoke strong emotions.
The Fat Bob features the 1,868cc Milwaukee-Eight V-twin that makes a commendable amount of power and torque. Out on the move, it’s also reportedly very easy to lay the power down. But even if you keep that aside, the Fat Bob 114 will manage to leave an impression in plenty of other ways, too. Genuinely fitting evolution for one of Harley’s most legendary models.
Harley-Davidson Fat Boy
Starting MSRP: $21,999
The Harley-Davidson Fat Boy is not just the coolest Harley-Davidson of all time but probably the most glamorous motorcycle ever. The beefed-up front forks and solid cast wheels let you know that this is one tough bike.
Showa suspension front and rear make it a joy to ride, and the mighty Milwaukee-Eight expertly fits in with the dominant heritage of the Fat Boy. Making an appearance in Terminator 2 solidified the old-school Fat Boy as the coolest Harley-Davidson ever.
Harley-Davidson Street Glide
Starting MSRP: $21,999
These days, the Street Glide is the quintessential Harley. Its iconic silhouette is synonymous with rebel culture and reckless spirits, living life their own way.
Powered by the beefy Milwaukee-Eight motor, the Street Glide makes every ride an event. Capable of long-haul trips, downtown cruises, and anything in between, the Street Glide is the ultimate modern Harley-Davidson. Plus, if the standard 107 cubic inch motor doesn’t quite cut it, the gargantuan 131 cubic inch behemoth is also an option.
Harley-Davidson VRXSE Screamin’ Eagle V-Rod Destroyer
Value: Up to $32,000
This outrageous creation by Harley-Davidson was all about getting a move on. And quickly. It reportedly had a top speed of over 140 mph. As you might have guessed, the VRXSE Screamin’ Eagle V-Rod Destroyer, mouthful though the name is, was destined for the drag strip.
Harley’s CVO team was the brains of this operation, and the VRXSE Destroyer could reportedly demolish the quarter-mile in under ten seconds. Its 60-degree V-twin Revolution engine made an absurd amount of power, and all in, it definitely deserves a spot on this list.
Harley-Davidson XR750
Value: Upto $48,000
A great example of Harley’s versatility comes in the form of the Harley-Davidson XR750. They built this motorcycle with one thing in mind — flat-track racing. The motor was based on the 883cc ironhead from a Sportster, although it had a shorter stroke.
The XR750 went on to win the most races in American Motorcycle Association history, claiming 29 out of the 37 championships from 1972 to 2008. So next time someone says that Harley-Davidson only makes cruisers, point to the brilliant XR750!
Harley-Davidson WLA
Value: Upto $52,000
One of the coolest and most important American motorcycles is the Harley-Davidson WLA. Based on a civilian motorcycle, the WLA was explicitly created for the US military during World War II.
Additional equipment included a luggage rack to carry radios, blackout lights to reduce visibility at night, a sub-machine gun holster, a skid plate, and crash bars. Usually finished in olive drab with a blacked-out motor, the WLA was a bona fide war veteran.
Harley-Davidson VR1000
Value: Upto $100,000
Harley-Davidson’s unicorn, the VR1000, had to make it to this list. In essence, it’s a Harley superbike, so how could it not?
This very cool-looking machine by the American manufacturer was designed to take on the might of Japan’s big four, and to bridge the gap, Harley-Davidson got plenty of help from outside its own engineering team. The likes of Buell, Roush, and even Cosworth spun their magic and brought the VR1000 to life. In the end, it wasn’t everything it could be because it lacked in a few key areas. Even then, as far as cool Harleys go, the VR1000 is right up there with the best.
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