The Most Legendary Harley-Davidsons (and 5 Duds)

The past decade was tough for Harley-Davidson. Sales have fallen; CEO Matthew Levatich stepped down in early 2020; and even before the market chaos of the coronavirus Harley stock was languishing. But nothing can tarnish its legendary status among motorcycle makers and its generations of loyal riders. In fact, one longtime company employee was recently taken to his final resting place on one.  Milwaukee-based Harley-Davidson has been making bikes since the early 20th century, and many are American classics. Here are some of Harley-Davidson's most iconic machines — with a few duds thrown in for good measure.

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You can't write about legendary Harleys without including early models such as this. The 11F was the first model to have a mechanically driven oil pump as well as a three-speed sliding gear transmission, which changed the game. These still occasionally go up for auction; one sold on Sotheby's in 2017 for more than $48,000. The listing notes the original price was $275 (adjusted for inflation, that’s about $8,100 in today’s dollars).

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If you were asked to imagine a vintage Harley, it probably would look something like the Model E. This piece of machinery was the first to feature what is known among Harley enthusiasts as the knucklehead engine. Though this engine was used on Harleys only through 1948, its influence was far greater than the figure would imply — it formed the basis for all Big Twins made since.

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Its production disrupted by World War II, this bike never quite got the due it deserved. The company shifted output to military motorcycles just as the WLDR was becoming popular. Before that happened, though, legendary motorcycle racer Babe Tancrede won the 1940 Daytona 200 riding one of these bikes, a race that went down in the history books for its challenges: 77 racers began the race, and only 15 completed it. 

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This motorcycle deserves its place in Harley (and American) history. Based on the civilian WL model, it was built to Army specifications (hence the "A" in its name) from 1941 to ’45 and used by the U.S. military and our allies during World War II (also later for the Korean War). It acquired its nickname, Liberator, after soldiers rode it into occupied Europe as the war came to an end. 

In 1958, Harley-Davidson redesigned the FL Hydra-Glide, introducing a rear suspension with a swingarm and twin shocks (hence the "duo" in the name). The original was a gorgeous bike, but the 1964 model, dubbed the Panhead, took it to new aesthetic levels, giving it the functionality — windshield, hard luggage compartments, etc. — of a touring bike.  

Anyone over a certain age will recognize this bike from the film starring Peter Fonda and Dennis Hopper. What many don't know is that the bike in "Easy Rider" was built by Fonda, bike customizer Tex Hall, and actor Dan Haggerty, starting with the base of a 1952 Harley-Davidson Hydra-Glide model that Fonda bought at auction. The Captain America chopper was crashed in the movie's final scene, then rebuilt by Haggerty. It was auctioned off in 2014 with a final bid of $1.4 million. 

The Electra Glide supplanted the Duo-Glide in 1966 after Harley introduced an electric start feature (you could still kick start the bike if you were a purist) and the more powerful shovelhead engine. But it wasn't until 1969 that the company introduced the batwing fairing (the aerodynamic shell), a feature that would become standard two years later and synonymous with Harley-Davidson design.  

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In production until 2009, with a 2014-2016 resurgence, the Low Rider is a Harley-Davidson contemporary classic. It was introduced in the late 1970s, aimed at the burgeoning aftermarket customization trend. Common modifications included lowering suspensions and adding low-slung seats and pull-back handlebars, so Harley decided to offer bikes with these features straight from the factory floor. In its first year of production, it outsold all other Harley models. 

Even if you've never been on a motorcycle, you've probably heard of the Fat Boy. It was, said a former Harley executive quoted in the Milwaukee Wisconsin Journal-Sentinel, "one of the coolest bikes that Harley ever introduced" and to this day remains one of the company's most iconic models. 

Introduced in 2001, this Harley is a drag-racer’s dream, with a high-revving engine and a spin-happy rear tire. When the V-Rod debuted, Motorcycle Cruiser magazine noted that it proved the company didn't just think "outside the box ... it blew the box away." The review went on to say, "The V-Rod certainly doesn't fall anywhere near the various niches Harley has created previously, and it forces us to expand our thinking about what a Harley can be technologically, aesthetically, and functionally." 

The Screamin' Eagle V-Rod is something to look at. Riders love its muscular acceleration and impressive handling. It was made in limited edition (just more than 2,200) for just one year by Harley-Davidson's Custom Vehicle Operations team, in three color combinations: black and electric orange, charcoal slate and scarlet red pearl, and chrome yellow pearl and platinum pearl. 

This bike has made a few lists of Harley's worst motorcycles because of its awkward design and poor performance. A 2006 New York Times article noted that the Sportster was "losing its punch" as early as 1973, "quickly falling behind sophisticated, extremely powerful Japanese bikes like the four-cylinder, 900 cc Kawasaki Z-1." 

Clearly, 1981 was not a banner year for Harley-Davidson. This bike, named to several critics’ lists of the company's worst, is notoriously low on power and off-balance, causing riders to tip to the left. This specific model year was made during the famously low-performing decade that AMF ran Harley-Davidson. It should be noted that the 1981 model was but a blip over a history of more than 50 years — the XR750 is otherwise noted consistently as one of the legendary vehicles of flat-track racing.  

This era of Harley's history is known for problems with the company's V-Twin engine. The specific issue with the 2001 Ultra Classic was that its engine used plastic parts that wore out disconcertingly quickly, with some models requiring repairs after just 15,000 miles or so. 

While other models are well loved, the 2014 Electra Glide is not, largely because it was plagued by issues with the engine and brakes. Those problems led to a major recall effort in 2014; in total there have been five recalls of this model.

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For 25 grand, you could buy this electric motorcycle that runs for only about 50 miles on one charge (something that takes up to four hours). So much for life on the open road. The 2020 version got better stats, but was priced even higher at nearly $30,000. In an effort to ride into the future, Harley-Davidson plans the brand to eventually be all-electric.

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