Harley-Davidson 1969 ‘Easy Rider’ Captain America Chopper
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11 Legendary Harley-Davidsons (and 5 Duds)

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Harley-Davidson 1969 ‘Easy Rider’ Captain America Chopper
Mario Tama/Getty Images

The Whole Hog

The past decade was tough for Harley-Davidson. Sales have fallen; its 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. Milwaukee-based Harley-Davidson has been producing 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.

Related: 75 Brands That Are Still Made in America

1915 Harley-Davidson 11F
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Legendary: 1915 Harley-Davidson 11F

You can't write about legendary Harleys without including early models such as this one. 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 $7,000 in today’s dollars).

Related: 23 Sports Collectibles That Scored Big at Auction

Harley-Davidson 1936 Model E
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Legendary: 1936 Model E

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, it's been noted that its influence was far greater than the figure would imply, forming the basis for all Big Twins made since.

Related: 20 Classic Italian Sports Cars We Wish Were in Our Driveway

Harley-Davidson 11941 WLDR
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Legendary: 1941 WLDR

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.

Related: From Bootleggers to Checkered Flags — The History of NASCAR

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Harley-Davidson 1942 WLA "Liberator"
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Legendary: The 1940s WLA "Liberator"

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 both 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.

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Harley-Davidson 1958 Duo-Glide
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Legendary: The 1958 and 1964 Duo-Glides

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.

Related: 22 Best Motorcycles for Weekend Warriors

1903 — Harley-Davidson
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Legendary: 1969 ‘Easy Rider’ Captain America Chopper

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.

Related: 32 Legendary Vehicles From '70s and '80s TV Shows

Harley-Davidson 1969 Electra Glide
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Legendary: 1969 Electra Glide

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 would also become synonymous with Harley-Davidson design. What replaced the Electra Glide, you might ask? Nothing; it's still being produced.

Related: 16 Epic Motorcycle Rides Across America

Harley-Davidson 1977 FXS Low Rider
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Legendary: 1977 FXS Low Rider

In production until 2009, with a brief resurgence in 2014 to 2016, 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.

Related: 15 Classic Car Models That Were Resurrected

Harley-Davidson 1990 FLSTF Fat Boy
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Legendary: 1990 FLSTF Fat Boy

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

Related: The 50 Greatest American Inventions of the Past 50 Years

2006 Harley-Davidson VRSCA V-Rod
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Legendary: The VRSCA V-Rod

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."

Related: 34 Companies That Changed American Culture for Better or Worse

Harley-Davidson 2006 VRSCSE2
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Legendary: 2006 VRSCSE2

The Screamin' Eagle V-Rod is something to look at. Riders love its muscular acceleration and impressive handling. It was produced 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.

Related: 23 Places to Get Behind the Wheel of a Sports Car You Can't Afford

Harley-Davidson 1981 Sportster
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Dud: 1981 Sportster

This bike has made a few lists of Harley's worst motorcycles ever made because of its awkward design and poor performance. But 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."

Related: 50 of the Smallest Cars Ever Made

Harley-Davidson 1980 XR-750
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Dud: 1981 XR-750

Clearly 1981 was not a banner year for Harley-Davidson. This model, named to several critics’ lists of the company's worst bikes, is notoriously low on power and off-balance, causing riders to tip to the left. This bike was made during the famously low-performing decade that AMF ran Harley-Davidson.

Related: 15 Historic Failures by Successful Billionaires

Harley-Davidson 2001 Ultra Classic
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Dud: 2001 Ultra Classic

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.

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Harley-Davidson 2014 Electra Glide
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Dud: 2014 Electra Glide

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 of 45,000 bikes in 2015; in total there have been five recalls of this model.

Recall: 15 Dangerous Products That Had to Be Recalled

Harley-Davidson 2020 Project Livewire Electric Motorcycle

Dud: 2017 Project Livewire Electric Motorcycle

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 help stave off continued corporate losses, Harley-Davidson plans to offer a full lineup of electric vehicles over the next few years, including ebikes.

Related: 15 Reasons I Drive An Electric Car