MoneyINC Logo
Years of

The 10 Best Harley Davidson Cruiser Models of All-Time

Harley Davidson Dyna Street Bob

The American motorcycle manufacturer we know today as Harley-Davidson, Inc. has its roots starting as far back as 1901 out of Milwaukee, Wisconsin when a twenty-year-old William Harley drew up plans for a small engine on a regular pedal bicycle. This small engine featured a displacement of just over seven cubic inches and four-inch flywheels. When he and his friend, Arthur Davidson, brought the plans of the bike into development, it took two years to finish this project.

In 1903, thanks to the help of Arthur's brother, Walter Davidson, the first motorcycle created by Harley and Davidson was ready for testing. When it was learned its ability to climb hills without pedal assistance, it was back to the drawing board to improve upon its design. In 1905, an improved version of the first Harley-Davidson motorcycle was introduced to the American market in limited quantity, which resulted in the first factory to be built in 1906 in what is now downtown Milwaukee.

Today, it is the official headquarters of Harley-Davidson, Inc. as the stretch of time, plus the technological advancements that have been made, have allowed the company to expand from its humble Wisconsin routes to feature several of its own shops, garages, and factories worldwide. Harley-Davidson is only one of two major motorcycle companies that managed to survive the ordeal of the Great Depression, along with the Dirty Thirties, that ravaged America clean through the 1930s.

Harley Davidson Cruiser Models

Harley Davidson, as a whole, did more than merely survive the Great Depression, as well as a number of ups and downs that have affected American businesses. Over the stretch of time, they have thrived to become a leading, world-class manufacturer of motorcycles that receives the level of respect it deserves. Already established as the king of producing customizable motorcycles for the rider, they are also best known for cruiser class two-wheelers. There are ten models in particular that stand out, which is seen in the list provided in this article.

Sportster Forty-Eight

10. Sportster Forty-Eight

In 1948, Harley Davidson introduced the Sporster Forty-Eight as the latest member of its motorcycle roster. Also dubbed as "Peanut," because of the design of its tank, this model would lead to the inspiration of Harley Davidson's entire roster of Sportster models that have continued to rule the roads as a two-wheeled masterpiece of vehicular design.

The Forty-Eight series was the most prominently featured motorcycle seen on various Hollywood productions, both on the small screen and big screen. Even when not glamorized on film, the road presence of this bike put all motorists on notice there is a beefy, mean, riding machine that always stands out from the crowd. This legendary breed of Harley Davidson motorcycles continues to have modernized versions of it in production. Feeling nostalgic, Harley Davidson has brought back the closest version of the original Sportster Forty-Eight lineup it can get while still working with the technological improvements the world has access to today.

1990 FLSTF Fat Boy

9. 1990 FLSTF Fat Boy

One of the most beloved motorcycles of all time, and not just with Harley Davidson, is the FLSTF Fat Boy. When the series made its debut in 1990, it came with an incredible amount of fanfare. It was introduced with all-new 16-inch wheels for its front and back, and it was solid. The silver elegance of the motorcycle's paint job also featured subtle yellow highlights that seemed to electrify the overall beauty of this two-wheeled machine.

The flared fenders added to the bike's appeal, as well as the 1337 cc air-cooled four-stroke V-Twin OHV engine, which was capable of a 48 horsepower output. When it was announced 2017 would be the final year the FLSTF Fat Boys would be discontinued to make way for the FLFB/FLFBS models that would start in 2018, old-school fans reacted as if they just lost their best friend.

2009 FXSTB Night Train

8. 2009 FXSTB Night Train

Well established as a six-speed cruising motorcycle for amazing performance, the 2009 FXSTB Night Train delivered a 1584 cc Twin-Cam 96B engine capable of putting out 87.9 lb-ft of torque at 2,500 RPM. The desirability of this Night Train model was the feeling of freedom on the road that was just as important for riders as its speed capabilities. The extended front end is credited for this it allowed a comfortable riding posture that contributed toward the rider feeling comfortable and free. The black coat that was laid out throughout the bike also made the FXSTB Night Train stand out as one of the most elegant motorcycles to grace the road.

1990 FLSTF Fat Boy

7. 2009 FLHT Electra Glide Standard

With a Twin-Cam V-Twin motor with Electronic Throttle Control (ETC), plus the trustworthiness of its engine, made the 2009 FLHT Electra Glide Standard one of Harley Davidson's most beloved motorcycles of all time. This bike featured a four-stroke engine that was capable of a 96.6 lb-ft torque at 3,500 revs per minute with its 1584 cc air-cooled engine unit. This six-speed cruiser served as an ideal along with haul motorcycle and is still regarded as one of the most stable Harley Davidson motorcycles the company ever built.

2007 XL1200N Sportster Nightster

6. 2007 XL1200N Sportster Nightster

Harley Davidson's 2007 XL 1200N Sportster Nightster is best known for its performance, despite its unique physical appearance that featured a bobbed rear fender, front fork gaiters, and a side placement of the license plate. The air-cooled rubber-mounted 1200cc Evolution V-Twin powertrain featured an Electronic Sequential Port Fuel Injection (ESPFI) system. The sturdy engine featured a 5-speed transmission, making it a versatile cruiser during its four-year production run.

2002 VRSCA V-Rod

5. 2002 VRSCA V-Rod

At the time, the V-Rod was the fastest Harley Davidson motorcycle made to date. This blasted open doors for drag racing opportunities, which is reminiscent of the brand's infamous past. The perfect combination of top-quality performance, as well as the custom styling Harley Davidson is well known for, became the official benchmark in the motorcycle world. The launch of the 2002 VRSCA V-Rod caused the world of motorcycles to sit up and take notice, thanks to its powerful 1130 cc, 115 horsepower beast of a machine, and 74 ft-lb torque. In 2002, a motorcycle achieving a speed of 140 miles per hour was an amazing feat. It was a first for a Harley Davidson brand, and it raised the bar for the company's competitors to keep up.

2006 VRSCSE2

4. 2006 VRSCSE2

The Harley Davidson Custom Vehicle Operation (CVO) team birthed the 2006 VRSCSE2 Harley Davidson powerful cruiser motorcycle that featured a series of modifications to the engine to make it perform even better than before. As beauty and beast in the form of a two-wheeled machine, the power it features comes from the Screamin' Eagle 1247 cc Revolution Engine that belts out 123 horsepower, which is associated with the fastest Harley Davidson model ever made, the V-Rod Destroyer. In addition to its powerful output, the VRSCSE2 looked like a motorcycle that just stepped out of the beauty parlor with three different color combinations for interested riders to choose from. Between charcoal slate with scarlet red pearl, platinum pear with chrome yellow pearl, or black with electric orange were the colorful canvases to choose from.

2012 FLHR Road King

3. 2012 FLHR Road King

The 2012 FLHR Road King earned its merit as an iconic Harley Davidson brand when it made its debut in 1994. Becoming the benchmark name, not just for Harley Davidson, but a nickname other motorcycle manufacturers borrowed, the six-speed cruising Road King boasted a punch of 103 horsepower and a 1690cc Twin-Cam. Ideal as a long-distance cruising bike, the full array of premium features such as the ABS mechanism, adjustable touring rear suspension, and electronic cruise control. The windshield was also removable, so the rider has the option to either enjoy the smooth ride with or without the wind-to-face experience.

2008 Harley Davidson Dyna Wide Glide

2. 2008 Harley Davidson Dyna Wide Glide

Officially classified as the FXDWG Dyna Wide Glide upon its introduction in 1993, this was measured as the longest motorcycle, as well as the most unique compared to the rest of its Harley Davidson relatives. The Tommy Gun 2-1-2 exhausts, larger back end, and chopped rear fender distinguished this model's appearance from all the other Dyna.

It also had a lower seat placement, allowing a gliding feeling that felt freer for the rider. From 2008 until 2017, this breed from the Dyna series became immensely popular, thanks to Sons of Anarchy, the critically acclaimed series that ran from 2008 until 2014. In some cases, the Dyna models were even more popular than the actors who rode them in the show.

Harley Davidson Dyna Street Bob

1. Harley Davidson Dyna Street Bob

Among the many motorcycle critics and fans, the Harley Davidson Street Bob is one of the highest regarded motorcycle cruisers on the market today. The Street Bob brings forth the basic roots of what made Harley Davidson one of the elite motorcycle manufacturers of all time. The distinguishing characteristics of the Street Bob feature the cutback rear fender, mini-ape handlebars, and the classic sizing, ride position, and styling the Harley Davidson brand is trademarked for.

It also has an air-cooled Twin Cam 103 engine which is powerful enough to slightly rumble the mirrors. The single-seat design makes the Street Bob a true cruiser motorcycle as it eliminates the worry of the passenger sliding off when twisting the throttle. Like the rest of the Dyna series, the Street Bob's popularity spiked thanks to the critically acclaimed series, Sons of Anarchy. In fact, the series is credited for saving the motorcycle industry from what had been a decline in popularity and sales due to stigmas that plagued it.

You can also read:

Benjamin Smith

Written by Benjamin Smith

Benjamin Smith is one of the managing editors of Moneyinc. Ben's been focusing on the auto and motorcycle sector since 2005. He's written over 1000 articles in the space and continues to learn about it each day. His favorite car is "any Bugatti" and he's a die hard Harley Davidson fan.

Read more posts by Benjamin Smith

Related Articles

Stay ahead of the curve with our most recent guides and articles on , freshly curated by our diligent editorial team for your immediate perusal.
As featured on:

Wealth Insight!
Subscribe to our Exclusive Newsletter

Dive into the world of wealth and extravagance with Money Inc! Discover stock tips, businesses, luxury items, and travel experiences curated for the affluent observer.
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram