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.

UPDATE: 2024/02/21 00:56 EST BY RAUNAK AJINKYA

Harley-Davidsons are known for a lot of things, but their motorcycles also embody an irrepressible coolness about them. There have been lots of them over the years, so we've updated this list to include a few more entries worth talking about.

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.

How we got our model selections: To compile this list, HotCars did a deep dive into the history of Harley-Davidson's motorcycles. The ones that made it to this list all have standout qualities about them, be it an undeniable road presence, an unprecedented take on an established segment, or simply something that drew universal appeal. It should be noted that this list includes both motorcycles currently in production and those that can be picked up from a used lot. Lastly, the motorcycles here have been organized in increasing order of their value.

14 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Harley was trying to evolve at the turn of the millennium, and they feared that their air-cooled V-twins might be outdated.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.

2003 Harley-Davidson V-Rod Specs

(Specs sourced from Motorcycle Specs)

13 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.

1970 Harley-Davidson FLH Electra Glide Specs

(Specs sourced from Motorcycle Specs)

12 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.

2012 Harley-Davidson FLHR Road King Specs

(Specs sourced from Motorcycle Specs)

11 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.

1986 Harley-Davidson FXR Super Glide Specs

(Specs sourced from Motorcycle Specs)

10 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.

2020 Harley-Davidson FXDR 114 Specs

(Specs sourced from Motorcycle Specs)

9 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.

2024 Harley-Davidson Sportster S Specs

(Specs sourced from Harley-Davidson)

8 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.

2023 Harley-Davidson Pan America Specs

(Specs sourced from Harley-Davidson)

7 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.

2023 Harley-Davidson Fat Bob 114 Specs

(Specs sourced from Harley-Davidson)

6 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.

2024 Harley-Davidson Fat Boy Specs

(Specs sourced from Harley-Davidson)

5 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.

2023 Harley-Davidson Street Glide Specs

(Specs sourced from Motorcycle Specs)

4 Harley-Davidson VRXSE Screamin' Eagle V-Rod Destroyer

Value: Upto $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.

2009 Harley-Davidson VRXSE Screamin' Eagle V-Rod Destroyer Specs

(Specs sourced from Mbike)

3 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!

1972 Harley-Davidson XR750 Specs

(Specs sourced from Motorcycle Specs)

2 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.

1954 Harley-Davidson WLA Specs

(Specs sourced from Motorcycle Specs)

1 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.

1994 Harley-Davidson VR1000 Specs

(Specs sourced from Motorcycle Specs)

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• Source for features: Harley-Davidson
• Sources for technical specifications: Motorcycle Specs and Harley-Davidson
• Source for used prices and auction values: Cycle Trader, Hagerty, Mecum