The Best Harley-Davidson's Ever Made [2023 Edition]

Why We Picked It:

In a choice that should surprise exactly no one, this list starts off with one of the most significant motorcycles that Harley-Davidson ever made. The 11J model was a very popular motorcycle, but sold for a staggering $310, making it out of reach for even some wealthy customers, and mostly because of its headlight.

Harley-Davidson made the choice to remove the complicated electrical headlight and replaced it with an acetylene-burning version. Yes, in those days you had to actually light your headlights. Named the 11F, it sold for a stupendous $35 less than the 11J, and put it much more in reach of many customers.

Those customers loved their bikes, as it had a slick three speed hand shift transmission, a mechanically driven oil pump, and the best part of all, it had 2 more horsepower than the 11J, jumping from 9 HP to 11 HP, from its 1,000cc V-twin. Harley-Davidson were so proud of the bike and the advancements made for it that with each bike sold, they signed a certificate that guaranteed the engine would provide all 11 of those horses.

Why We Picked It:

Think about the time period that this bike came out in. After the Great War and at the tail end of the Great Depression, motorcycle companies had gone under in droves, with only Indian Motorcycles and Harley-Davidson having weathered the storm. Yet, Indian was pulling ahead in sales, as their bikes were faster and much more reliable.

Harley-Davidson engineers thus got together and narrowed down what really drove reliability: Lubrication and efficient combustion. Dry sump technology was still new at the time, and William Harley knew that the sidevalve big-twin debacle of the previous years meant that change was needed.

The solution was to mount the valves on the top of the cylinders, but to make room for them and the cams, the heads of the V-twin would need to be lifted and shaped. The new "Overhead Valve" system worked a treat, but the new engine leaked so much oil that the bike almost didn't make it to market. However, solutions were found, and with the distinctive shape of the cylinder heads, the famous Knucklehead V-twin was born.

Why We Picked It:

If this list did not have the WLA Liberator in it, it wouldn't be complete, simple as that. It was one of the USA's most significant contributions in terms of vehicles to the European theater of war, with over 10,000 being shipped over. It was tough, reliable, could be fixed with a hammer and a very emphatic curse word, and could ride on almost any surface.

They were not used for front line service, instead being used for courier duties, military police patrols, and escort duties. It was especially in the courier duties that it paid dividends, as the streets and roads of Europe in the 1940s were often tight, twisting, and narrow, and whereas a Willis Jeep might get stuck, the WLA Liberator could snake its way through and get the messages, documents, or other items through quickly and reliably.

After the war ended, many of the bikes that came back to the USA were bought up by soldiers and converted for civilian use, making the original olive green paint job with the stenciled white star on the tank exceedingly rare. Nowadays, they are mostly in private collections or museums, where they can be appreciated for what they are.

Why We Picked It:

The saying goes that beauty is in the eye of the beholder, but to pretty much anyone that beholds a 1949 Harley-Davidson Hydra Glide Panhead, beauty is defined. It is a simplistic motorcycle, with very little in the way of fairings or even panels. It has a mudguard over each wheel, a tank, a saddle, a frame, and a big chunky V-twin slung low and forward.

It is simple, but it also is perfect. Every angle, every line, every curve, just everything about it is beautiful. No muss, no fuss, no frills, no extraneous flairs or such. From any angle, from every angle, it is the definition of American iron, the image that most non-riders have of an American cruiser when you ask them to point one out in a lineup.

Yet, it was also significant in that it carried the all-new panhead engine, an evolution of the knucklehead. With the oil leak problem fixed almost a decade ago, the biggest thing about the panhead was that it introduced two very important technologies which are still used, in a modified form of course, today.

Those technologies were the pushrod activated valves that gave it the now-classic burble we think of from Harley V-twins, and the hydraulic self-adjusting tappets, which constantly adjusted the valve spacing instead of having to disassemble the engine every 10,000 miles to adjust them manually. In effect, if a panhead engine is maintained properly, it will run forever, and many that are still running today have not had their valves manually adjusted at any point.

Why We Picked It:

Throughout the years, the FL line of motorcycles from Harley-Davidson have carried important innovations, upgrades, and ideas, but the 1965 Electra Glide was the most significant of them all.

Apart from being the last bike to carry the panhead V-twin, and the "Big Twin" version of it at that, the Electra Glide's contribution to Harley history is it being the first model to carry an electric starter. It was also be argued that the Electra Glide was the first fully touring-oriented motorcycle, as it had a massive 5 gallon "Turnpike" tank fitted, and had accessories available that included saddlebags, a full windshield, and the like.

The other significant upgrade that the Electra Glide received was a 12 volt battery, up from the standard 6 or rarer 9 volt batteries used to date. It needed the extra juice for the starter, but it also allowed for a powerful headlight to be fitted for nighttime riding, another innovation for long-distance touring.

While a full touring motorcycle wouldn't be officially created until the "Tour Glide" models such as the 1971 Super Glide, it was the Electra Glide that set the standard and forged the path for one of Harley-Davidson's more popular niches today.

Why We Picked It:

While originally designed to be a racing bike, the 1970 Harley-Davidson XR-750 flat track racer is famous for an entirely different reason. Those that grew up in the 1960s and 1970s bore witness to a madman in a crash helmet and a star spangled outfit, the tank of his bike painted in the stars and stripes, and they would often see this man soar over busses, bridges, rivers, and pretty much anything else that could be jumped. The XR-750 is famous because of Evel Knievel.

Sporting a 748cc air-cooled V-twin, the XR-750 put down a respectably 82 HP and weighed only about 310 lbs wet, making it one of the lightest bikes Harley-Davidson made. It also was very well sprung in terms of suspension, although daredevils would add a little more suspension travel and damping, as it was designed to have the tail kicked out and be sliding sideways around a bend, so it couldn't be too stiff as that could cause the rear tire to dig in and flick the rider off in a highside.

From 1970 to 1976, Evel Knievel successfully jumped his XR-750 multiple times, including his longest jump at the time of 129 feet over 19 cars. He crashed his original XR-750 in 1975 when attempting to jump 120 feet over 13 busses, but five months later, on another XR-750, he set the world record that stood for 25 years of 133 feet over 14 busses.

Demand for a street legal version was met with a slow response from Harley, although they did eventually release a version of it as the XR-1000 Sportster. It was too late, however, as better bikes had come along by then, so it has been chalked up as one of H-D's biggest misses.

Why We Picked It:

If anything in 1990 screamed "AMERICA," it was the Harley-Davidson Fat Boy. Based on an 82 ci V-twin softail, Wille G. Davidson, with assistance from Louie Netz, absolutely nailed the stance, the grunt, the poise, and the power that people associated with American iron, and in many respects the USA itself, around the world. It was quite literally a bike that you could show anyone in the world, and no matter where you were, they would say "That's American."

Of course, a lot of the world was able to see exactly what the solid-wheeled chunky bike was all about in 1991, as it was the hero vehicle of a cyborg in a small movie called Terminator 2: Judgement Day. All of a sudden, the rumbling burble of Harley-Davidson was the soundtrack to some of the best action and chase sequences in the summer blockbuster season that year.

On that note as well, when a motorcycle can make even Arnold Schwarzenegger look positively average astride it wearing sunglasses at night, you know it's a big, fat bike that just oozes cool.

Why We Picked It:

The FXR CVO models are not often brought up in the "Best Harley's Ever Made" lists around the internet, and we are left scratching our heads as to why. In 1999, the Harley-Davidson FXR Dyna had already been out of production since 1995, yet many customers still loved the bike and asked when a new version would be coming out. This was also around the time that the aftermarket and custom bike scene started to really gain steam in mainstream media, and so Harley created Custom Vehicle Operations to start making a "new" FXR, but with about $4,000 worth of custom parts added to each one.

It was the second generation of the FXR customs, the FXR3 CVO, that really grabbed people's attention. With 900 FXR2's and 900 FXR3's, the limited edition nature of the bikes garnered attention, although many wait to see what the first version would be like. It was built around the 80 ci Evolution V-twin, which had rubber bushings on its mounts to smooth out body vibrations, and a very taut and stiff frame so that it handled more like a Sportster than a Dyna.

But what is a custom Harley without a two tone flame paint job on the tank? Only the FXR3 CVO's had them, as well as the new 5 spoke cast ThunderSTar wheels, a new and bespoke seat just for the FXR3, taller sissybar than the Dyna, chrome trimmed sidecovers, and braided steel control cable and tubing sheaths.

As a limited edition version of what Harley-Davidson considered the ultimate custom, it deserves its place on this list for showing that they can, sometimes, go crazy in the best ways.

Why We Picked It:

We'll admit, the V-Rod may not have been the most popular or even the most desirable of Harley-Davidson's many models during the 2000s. However, it is significant because of the impact it made, and it also allowed a new word to enter into the lexicon: Performance.

Before 2002, if you wanted a "performance" Harley... you bought a Buell. However, because of providing engines for Buell for so long and refining them more and more, the Revolution V-Twin engine was made. Suddenly, this 1,130cc (69 ci) engine was chucking out 115 HP and 84 lbs-ft of torque, revving all the way up to 7,000 RPM, and tearing up the drag strip without needing any modifications.

It probably helped that the Revolution engine was developed with assistance from a small little company named Porsche from Germany, so every single inch of its 69 cubic inches of displacement were optimized for power and performance. It didn't sell quite as well in the USA and Canada as Harley hoped, but it was an absolute smash hit overseas, where people were celebrating it as a bike from America that finally had the performance to match its looks.

Why We Picked It:

For the longest time, unless you were a hardcore Harley-Davidson enthusiast, the bikes from Milwaukee were often seen as "old man" motorcycles, or midlife crisis items that were cheaper than a Porsche to buy but still cost a pretty penny. In effect, Harley-Davidson needed something to attract a new generation of riders with, something that would have them turn away from the Japanese and European bikes and go "hey, yeah, there is a good bike out of America I can ride."

That bike was the 2016 (discontinued in 2022) Iron 883. Based on the Sportster silhouette, it had all of the elements of a Harley, but brought bang up to date. It had all the electronics and rider aids a new rider wanted, it had comfortable midmount pegs, the bars were easy to reach, and it didn't weight two tons so it was agile and even flickable in the right conditions.

Despite being geared up to the teeth with rider aids, it also was pared back and stripped down in terms of information and controls. It was a bike you could learn riding on without having to focus on not hitting 17 different switches on the left button box. It communicated the road better than most Harley's at the time, and it definitely was a sports cruiser with is throttle response and noise.

It worked, too. All of a sudden, new riders were popping up all over the place astride their shiny new Iron 883s, and Harley-Davidson has kept that theme going with the new 2024 Nightster, which is targeted at the same new-rider crowd that are getting their licenses and looking to have a fun ride down the road of life.