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The Most Iconic Harley of Every Decade Since 1903

The Most Iconic Harley of Every Decade Since 1903

There are motorcycles, and then there are Harley-Davidsons. Imbued with a mystique that transcends motorcycle culture, Harley-Davidson has built an empire not just on good branding, but on unimpeachable quality and time-honored tradition. Telling someone you ride a Harley (or better still, learned how to ride on a Harley) is the bragging rights equivalent of telling someone you go to an Ivy League school — only it’s far less pretentious and carries way more street cred.

Harley-Davidson’s prestige is owed in large part to its storied past. Founded in 1903, the company has been churning out revolutionarily cool models for over 100 years, and it continues to set the standard for motorcycles today. Much has changed in the past century, but one thing hasn’t: Riding a Harley turns heads. Whether you’re into vintage bikes or the flashiest contemporary models, these are the most iconic Harleys of every decade since 1903.


1903 to 1910: Harley-Davidson Model 5 Series (1909)

Before motorcycles were a status symbol synonymous with masculinity, there were the early bikes that didn’t exactly look as flashy, or sound as loud, as today’s behemoths. That doesn’t make them any less important, however. It might appear simple at first, but the Model 5 series (consisting of the Model 5-A, 5-B, 5-C, and 5-D) was an iconic moment in the history of the company. Despite its simple design, the Model 5 series marked the launch of the brand’s V-Twin engine, which is a two-cylinder piston engine arranged in a V formation. Find one in good condition today and you might just have a fortune on your hands.


1910 to 1920: Harley-Davidson 11F (1915)

The 11F was Harley-Davidson’s first three-speed sliding gear transmission, which officially turned the company into a motorcycle brand rather than simply a motorbike brand. The 11F’s new (for the time) acetylene-burning headlight, mechanically driven oil pump, full electrical system, rear tail light, and the increased power of its 1000cc V-Twin engine made it one of the most innovative of the decade.


1920 to 1930: Harley-Davidson Model D (1929)

The Model D delivered big when it came to horsepower at the time with its 45 cubic inch flathead V-Twin engine. Key phrase for modern riders is “at the time,” of course. The two bullet headlights option is now an iconic symbol of bikes in the 1920s. The motorcycle came in at an affordable price point as well, which helped sales of the Model D during the Great Depression.


1930 to 1940: Harley-Davidson EL “Knucklehead” (1936)

When a motorcycle has its own time-honored nickname, you know it’s iconic. The EL “Knucklehead” was a staple of the 1930s and introduced riders to the overhead valve and a combustion chamber design. It also packed a punch in the horsepower department, and made an aesthetic impression with its fresh frame and fork design and a two-tone paint scheme. It was the first Harley to have an instrument cluster on the top of the tank, too, and quickly became one of Harley-Davidson’s best-selling bikes.


1940 to 1950: Harley-Davidson WR Racer (1946)

You probably wouldn’t win many races on the WR Racer today, but that doesn’t mean it wasn’t a force to be reckoned with in the past. Designed for Class-C racing, the bike was lightweight and powered by a 738cc V-Twin engine and three-speed transmission. Equipped with a full race trip, suicide clutch, and heavy-duty Wico magneto, it only lasted a few years before being replaced by a newer model, but not before making an impact on the ‘40s.


1950 to 1960: Harley-Davidson Hummer (1955)

Telling someone you drive a Hummer in the 1950s meant something completely different than it does today. Instead of a gas-guzzling behemoth of a vehicle, the 1955 Harley-Davidson Hummer was a basic motorcycle with a stripped-down look. An old-fashioned motorcycle without the bells and whistles, its simplicity was a statement in itself. The Hummer was named after Dean Hummer, a Harley dealer in Omaha, Nebraska. Not a bad reward for a successful sales track record.


1960 to 1970: Harley-Davidson Electra-Glide (1965)

The first FL Harley to feature an electric starter, the Electra-Glide was a powerhouse, at 800 pounds and 55 horsepower. It featured a 12-volt electrical system, a larger gas tank than previous models, and an optional “King of the Highway” package including hard saddlebags, a removable windshield, luggage rack, and chrome accessories. This model was also the first to make Harley-Davidson known as a “cop bike,” thanks to the classic film Electra-Glide in Blue.


1970 to 1980: Harley-Davidson XLCR 1000 (1977)

Though not exactly a stellar sales performer, the XLCR 1000 has earned a spot in Harley-Davidson history for its cafe-style bikini fairing, single racing seat, and dirt track tank grafted onto a Sportster frame. Only 2,000 were produced in 1977, making them a collectible today. Indeed, an original 1977 XLCR is worth over $20,000 for lovers of vintage Harleys. Its collectible status has made the bike something of a cult favorite.


1980 to 1990: Harley-Davidson FXRP (1985)

A special design derived from the popular FXR and put into widespread use by the police force, this was the ultimate Harley-Davidson cop bike. Though the standard version was also great for everyday touring, the police version came with panniers, ties, floorboards, and a special windscreen. Chrome pieces were also substituted with matte black paint, so they looked more official (and perhaps intimidating). Apart from its striking appearance, the FXRP’s precision handling and comfort really made the bike stand out among its contemporaries.


1990 to 2000: Harley-Davidson Fat Boy (1990)

If you’re a motorcycle enthusiast, fondly remembering the ‘90s is not just blind nostalgia. The Fat Boy, released in 1990, is perhaps the most iconic and widely-recognized Harley-Davidson of all time. Not only famous for its starring role in The Terminator, the Fat Boy was known for its silver-gray finish, solid disc wheels, “shotgun” exhausts, valanced fenders, FL-style front forks, and a 1,340-cc Evolution V-Twin engine. The model was so popular it’s still being sold today, and has influenced the design of several of Harley’s later models. There are even LEGO sets devoted to the Fat Boy, so if you’re not quite ready to purchase one, at least you can assemble one.


2000 to 2010: Harley-Davidson FXSTB Night Train (2009)

One of Harley-Davidson’s most iconic motorcycles ever made, the Night Train has more than just a cool name. From its classy look to its unmistakable bass sound, this motorcycle has all the bells and whistles Harley lovers have come to expect after 100 years. Designed for young and fit drivers (due to the low and slightly uncomfortable riding position) this is the ultimate rebel bike that’s particularly suitable for shorter trips and making an impression as you fly past crowds.


2010-2020: Harley-Davidson Switchback FLD (2016)

The Switchback FLD is equally as suited for cruising around town as it is taking a long cross-country road trip. Equipped with detachable saddlebags and a removable windshield, this motorcycle serves as a one-size-fits-all option for those looking to hit the road without really knowing where they’re going.