16 Best And Worst Years For Harley [High & Lows]

Harley-Davidson is a famous American motorcycle brand known for its innovative designs and long-lasting presence. 

Over the years, it has experienced success and challenges with its motorcycle lineup.

In this article, we will explore the best and worst years of Harley motorcycles and discuss their lasting impact on the world of motorcycles.

Best And Worst Years For Harley 

Harley-Davidson has experienced a series of highs and lows over its more than a century-long history. 

The best years of the Harley are usually considered the 2017, 1989-1999, 2006-2018, 1998-2010, 1993, 1995-2009.

However, the 2001, 1981, 2014, 2004, 2005, 1999 years are considered the worst and years to avoid for Harley.

Years To Avoid For Harley

These are the worst years for Harley motorcycles, which you must consider avoiding.

1. 2001 Ultra Classic

The 2001 Ultra Classic, is often considered a year to avoid. This model was plagued by a series of technical problems that tarnished its reputation. 

One of the main issues was with the Twin Cam 88 engine, which was notorious for its cam chain tensioner problem. 

The plastic shoes on the cam chain tensioners were prone to wear out and even disintegrate, leading to engine failures in some cases and requiring expensive repairs. 

Moreover, the 2001 Ultra Classic was also beset by design flaws, like its susceptibility to oil leaks and problems with the clutch.

These issues were further compounded by the bike’s relatively high maintenance demands, making it an unattractive choice for many Harley Davidson fans. 

2. 1981 Sportster

The 1981 Sportster is often regarded as one of the most troublesome models. One of the biggest problems with this model was that its gear-shifting system had a lot of trouble.

The 4-speed transmission was notoriously unreliable, often leading to missed shifts and breakdowns, significantly affecting riders’ experiences.

The 1981 Sportster was equipped with an Ironhead engine that, despite its power, was infamous for its high maintenance requirements. 

This engine was prone to overheating, resulting in a high frequency of mechanical failures that necessitated frequent and costly repairs. 

With its inefficient fuel system, these shortcomings made this model one of the least desired. This was a time when Harley Davidson was having money problems, and AMF had just sold it. 

Because of these changes, they didn’t check the quality of their bikes as much as they should have. 

This made the 1981 Sportster not as good as it could be. So, if you’re thinking of buying a Harley Davidson, it’s usually best to avoid the 1981 Sportster.

3. 2014 Electra Glide

The year 2014 was particularly infamous for Harley-Davidson due to the severe issues with the Electra Glide model. 

People were really excited about the 2014 Electra Glide and expected it to be amazing. 

But it ended up being a big letdown. There were many recalls and complaints from customers that hurt its image. One of the most significant problems was the clutch issue. 

The hydraulic clutch system in these motorcycles was prone to failure, causing riders to lose control of the clutch unexpectedly, posing serious safety hazards. 

Another concern was the overheating of the Twin Cam 103 engine, which led to decreased performance and increased wear and tear.

Moreover, the bike’s Infotainment system was frequently criticized for its complexity and unreliability. 

These issues, coupled with a high retail price, resulted in diminished consumer confidence and poor sales, making the 2014 Electra Glide a year to avoid.

4. 2014 HD Street 500

The Street 500, released in 2014, has been widely recognized as one of the least successful models produced by Harley. 

This model was a departure from the traditional Harley Davidson style, aiming to attract younger, urban riders. However, it fell short on several fronts.

Primarily, the Street 500 faced severe criticism for its subpar build quality and frequent mechanical issues. 

Many riders reported that it suffered from a rough idle, often coupled with stalling issues. The brakes, too, lacked effectiveness and durability, posing potential safety risks.

Further, the Street 500 was relatively underpowered compared to its competitors in the same price, offering a disappointing ride experience.

Its 494cc liquid-cooled Revolution X V-Twin engine, though designed for urban commuting, was found lacking in performance and trademark sound.

The model was controversial for its overseas production. Unlike traditional Harley models made domestically, the Street 500 was manufactured in India and Brazil for most markets. 

This decision was not well-received by loyal Harley enthusiasts who appreciated the brand’s American legacy.

Its slew of mechanical issues, coupled with questionable production decisions and poor performance, led to a disappointing year for one of America’s most revered motorcycle brands.

5. 1999 FXSTB Night Train

The Harley-Davidson FXSTB Night Train had a notably challenging year in 1999.

Despite its impressive aesthetic appeal with a glossy black finish and a sleek, streamlined look, the model fell short on performance and reliability. 

One of the significant issues was the Twin Cam 88 engine that came with the Night Train. 

While this engine brought more power, it also introduced a design flaw known as the “cam chain tensioner problem.” 

The plastic shoes that rode on the cam chains wear out prematurely, potentially leading to serious engine damage and expensive repair costs.

The Night Train was also equipped with a carburetor instead of fuel injection, which was common in motorcycles during that era. 

This outdated technology made the bike more difficult to start in cold weather and less fuel-efficient compared to its contemporary counterparts. 

Moreover, the motorcycle was known for its stiff ride and heavy steering, which was part of Harley’s traditional feel but was considered inconvenient by many riders.

Therefore, the 1999 Night Train is commonly seen as a model year to avoid for those considering a used Harley-Davidson motorcycle. 

6. 2004 Dyna Super Glide

The 2004 Dyna Super Glide is often mentioned in discussions about the worst years for Harley motorcycles. 

The key issue was the Twin Cam 88 engine, introduced in 1999, which was standard in all 2004 Dyna models. While powerful, this engine was notorious for its failure-prone cam chain tensioner. 

The tensioner worn out prematurely, leading to serious engine damage and costly repairs, which was a significant deterrent for potential buyers.

Moreover, the bike faced criticism for its poor aesthetic design. Many riders felt that the 2004 model lacked the distinct, classic Harley-Davidson look. 

There were also complaints about the uncomfortable riding position due to the poorly designed seat and handlebar placement.

Reliability was another major concern. The 2004 Dyna Super Glide was plagued with electrical issues that often resulted in malfunctioning indicators and headlights, posing safety concerns for riders. 

7. 2014 Livewire

The 2014 year was tough for Harley-Davidson as they launched the ‘LiveWire’ project. Sadly, this ambitious plan didn’t work out well.

LiveWire was Harley’s first electric motorcycle, a bold step into the future for a company renowned for its classic, gas-powered machines. 

However, the bike faced a slew of issues that have led many to consider it one of Harley’s worst ventures.

Firstly, the LiveWire came with a hefty price tag of $29,799, far more expensive than other electric motorcycles on the market. 

This steep price was a major deterrent for potential customers. Secondly, the bike’s limited range was another significant drawback. 

With a maximum range of just 95 miles in city riding conditions, the LiveWire fell short of competitor offerings, impacting its marketability.

Furthermore, the bike suffered from mechanical issues, including a global recall due to a charging-related problem. 

These problems got worse because Harley’s dealers weren’t ready to fix electric motorcycles. 

This led to poor service for customers. Plus, the LiveWire didn’t appeal to Harley’s usual customers who love the brand’s history with gas-powered bikes.

8. 2005 Softail Deluxe

The 2005 Harley Softail Deluxe is widely viewed as one of the worst years for Harley motorcycles due to a multitude of problems that plagued this model. 

The most prominent issue was the Twin Cam 88 engine, which was known to have significant reliability problems. 

Leaking oil was a common occurrence, often requiring costly and time-consuming repairs.

Another significant concern was the poor braking system. Riders complained that the brake response was sluggish and offered little stopping power.

The Softail Deluxe was also criticized for its uncomfortable seat and overall ergonomics. Many owners found the riding position to be awkward, leading to discomfort on long rides.

Furthermore, it was a matter of concern that the 2005 Softail Deluxe was not as fuel-efficient as its competitors or even other models in the Harley lineup. 

This, combined with the model’s high maintenance costs, made owning a 2005 Softail Deluxe an expensive proposition.

Best Years For Harley Motorcycles 

These are the best years for the Harley motorcycles that you must consider buying.

1. 1995-2009 Harley Dyna Glide

The 1995-2009 Harley-Davidson Dyna Glide is often considered the best year for Harley motorcycles.

The Dyna Glide is powered by a reliable 1584cc Twin Cam 96 engine, providing plenty of torque and a memorable exhaust note.

The worth of this model can be found in its excellent mixture of old-fashioned and contemporary design aspects. 

The famous Harley front look, combined with a stylish, narrowed back, evokes a sense of nostalgia. 

At the same time, modern features like the 6-speed Cruise Drive transmission bring a fresh feel to it.

Investing in these models offers a perfect blend of performance and heritage, with features such as fuel injection, front and rear disc brakes, and a hefty 5-gallon fuel tank. 

The robust suspension system ensures a smooth ride, even on less forgiving roads. However, what truly sets these versions apart is their unmatched customization potential. 

The removable rear subframe allows you to modify your bikes into a bobber or chopper style, further enhancing the Dyna Glide’s appeal.

2. 2017 Harley-Davidson Iron 883

The 2017 Harley-Davidson Iron 883 is a prized motorcycle among enthusiasts due to its plenty of specs. The Iron 883 is renowned for its raw, stripped-down, and aggressive style. 

Its look is simple, with lots of black and no extra decorations, giving it a strong and powerful feel. One of the major factors contributing to its value is the motorcycle’s performance. 

It is equipped with an air-cooled Evolution 883 cc V-Twin engine that delivers robust torque at low RPM, ensuring a smooth ride. 

The ESPFI system optimizes fuel delivery, thereby enhancing the performance and efficiency of the bike.

The motorcycle boasts a low seat height, a narrow frame, and a perfectly balanced suspension. 

This design allows for easy handling and excellent control, making it an ideal choice for city commuting and long-distance touring.

The 883 also features an adjustable rear suspension and front cartridge forks, providing riders with the ability to customize their ride to their style and preference. 

The motorcycle comes with optional ABS for enhanced safety and a security system, adding to its overall value.

In terms of accessories, the Iron 883 is equipped with a classic 3.3-gallon fuel tank, drag-style handlebar, machined 9-spoke wheels, and front and rear fenders that can be easily customized.

The 2017 Iron 883 is a perfect blend of timeless style, modern technology, and unparalleled performance, making it one of the most valuable models in the Harley lineup.

3. 1989-1999 Harley Fat Boy

The Harley-Davidson Fat Boy models produced between 1989 and 1999 are often celebrated as some of the most iconic and valuable motorcycles in the brand’s history. 

Fat Boy was introduced in 1989 and gathered attention for its unique design, solid-cast disc wheel, a bold choice that distinguished it from the laced wheels.

These Fat Boy models are powered by the legendary Harley-Davidson 1340cc V-twin engine, renowned for its robust and reliable performance.

The engine offers an impressive torque output, providing a thrilling ride that many motorcycle enthusiasts crave.

The Fat Boy got a lot of attention in movies and pop culture during these years. It became a sign of how important Harley-Davidson was in the world of motorcycles.

These years stood out because they had a timeless and bold look that captured the feel of that time. 

This makes it a treasured item for those who collect Harley-Davidsons and fans of the brand.

Beyond this, the Fat Boy maintained Harley-Davidson’s commitment to quality, with features like a Softail frame for a comfortable ride, premium suspension, and a sizable fuel tank for long cruising durations. 

These factors make the 1989-1999 Fat Boy models not just motorcycles but a piece of motorcycling history.

4. 2006-2018 Harley Night Rod Special

Harley-Davidson’s Night Rod Special, produced between 2006 and 2018, is often hailed as one of the best periods for Harley motorcycles. 

These models are highly valued for their sleek design, robust performance, and distinctive features that set them apart from other motorcycles in the same category.

The 2006-2018 Night Rod is powered by a liquid-cooled 1250cc Revolution V-twin engine that generates 125 horsepower and 85 ft-lb of torque, delivering powerful and smooth rides. 

This engine, combined with a 5-speed transmission, ensures a thrilling user experience, making these models stand out in the Harley lineup.

These models are also recognized for their unique aesthetic appeal. 

With their stretched-out, low-riding design, fat rear tire, and drag-style handlebar, these motorcycles radiate an aggressive yet sophisticated aura. 

The dual exhaust with satin chrome finish, along with the blacked-out powertrain and bodywork, bring an additional edge to these motorcycles’ style.

These models boast a number of high-end features, such as ABS and a standard security system, with options for cruise control and a smart security system. 

The 240mm rear tire provides enhanced stability and traction, while the inverted front forks and rear shock suspension ensure a comfortable yet sporty ride.

5. 1998-2010 Harley Night Train

The 1998-2010 Harley-Davidson Night Train holds a unique position in the annals of motorcycle history.

Its legacy rests not merely on its innovative design and superior performance but also on the unique charm that captured the hearts of motorcycle enthusiasts worldwide. 

The Night Train is a part of Harley’s Softail series, known for its blend of vintage looks with modern technology. 

The Night Train, however, took it a step further with its exclusive, blacked-out theme, giving it a distinct, raw, and aggressive look.

Every new model of the Harley-Davidson Night Train made each year came with improvements and tweaks. 

However, the core feature remained the same: its strong Twin Cam 88B engine. This was an air-cooled engine with two cylinders that had a capacity of 1450cc. 

It produced around 78.2 ft/lb of torque at 3500 revolutions per minute, providing a powerful yet smooth ride. 

The bike also had a Softail design and low, drag-style handlebars. This provided a comfortable position for the rider, making long trips less tiring.

The Night Train motorcycle is valuable because it’s rare. It was released as a special edition and quickly gathered a fan base. 

When it stopped being made in 2010, people wanted it even more. The bike’s specific features, along with its cool, dark image and lasting popularity, make it not just fun to ride but also a good investment.

6. 1993 Harley FLHR Road King

The 1993 Harley-Davidson FLHR Road King is often heralded as one of the best years for this iconic brand. 

Introduced to celebrate Harley-Davidson’s 90th anniversary, the Road King represented a return to the brand’s classic touring roots. 

The ’93 FLHR was powered by a 1340cc V-Twin engine, recognized for its robust power and torque. 

It featured a distinctively designed, retro fairing, a large and comfortable seat for long rides, hard saddlebags for ample storage, and wide handlebars for superior control.

This model was known for its basic, minimalist design that focused more on usefulness rather than looks, reminding people of Harley’s initial design approach. 

The mix of old-time feel and today’s performance made the ’93 Road King popular among Harley fans.

In terms of value, its significance as a 90th-anniversary model, the introduction of the Road King name, and its balance between classic and modern design elements make it highly desirable to collectors. 

Indeed, well-maintained examples can command premium prices in the used motorcycle market.

The 93 Road King embodies the timeless allure of the Harley-Davidson brand, making it a standout choice for any motorcycle enthusiast.

7. 1998-2005 Harley Super Glide Sport

Many riders see the 1998-2005 Harley-Davidson Super Glide Sport as a fantastic years of a motorcycle.

Among all Harley bikes, these models are viewed as the most valuable because they perform well, are comfortable, and look great.

During these years, Harley-Davidson made notable improvements to the Super Glide Sport, particularly in terms of engine performance. 

The bike was equipped with a powerful 88-cubic inch (1450cc) twin-cam motor, delivering an impressive torque of 78.2 ft-lb at 2900 rpm. 

This engine upgrade significantly enhanced the bike’s acceleration and top speed, making it a favorite among speed enthusiasts.

The Super Glide Sport also boasted a refined suspension system, which provided better handling and improved ride comfort. 

This was obtained by adding a 39 mm front fork with dual-rate springs and preload-adjustable rear shocks.

One aspect that set the 1998-2005 Super Glide Sport apart was its distinctive styling. 

The bike featured a minimalistic design with a stripped-down look, a solo seat, and a lack of overly decorative elements. 

This change from the usual fancy styles Harley-Davidson is known for making the bike more attractive to many riders. It had a rough, simple look that was modern yet classic.

Moreover, the Super Glide Sport was built with premium materials, ensuring its durability and longevity. 

Harley-Davidson’s commitment to quality production during these years has resulted in motorcycles that, even decades later, continue to perform reliably.

This is a key factor in their enduring value and desirability among motorcycle enthusiasts.

The 1998-2005 Harley Super Glide represents a perfect balance of power, comfort, and style, making these years the most prized in Harley-Davidson’s illustrious history. 

8. 2007 Harley-Davidson Sportster 1200 

The 2007 Harley-Davidson Sportster 1200 Nightster stands out as a remarkable highlight in Harley’s history. 

Its launch marked a notable shift in Harley’s design ethos, blending a retro aesthetic with modern performance.

This unique blend of old-school charm and contemporary function is a significant reason the 2007 Sportster is considered one of the best years for Harley motorcycles.

The Nightster’s value comes from its unique design elements. Its traditional 1200cc V-Twin engine gives a nod to the Harleys of the past. 

At the same time, its sleek, low-profile look, parts colored in black, and simple design give it a modern and cool appearance.

As for specs, the 2007 Nightster doesn’t disappoint. The engine delivers a robust 79 ft-lb of torque at 4000 rpm, ensuring a thrilling ride. 

It features electronic sequential port fuel injection (ESPFI), which guarantees optimal fuel delivery, enhancing performance and fuel efficiency. 

The bike’s raw-boned design is complemented by a low seat height of just 25.3 inches, making it accessible to riders of all heights.

All in all, the blend of unique aesthetics, strong performance, and accessible riding position make the 2007 Harley-Davidson Sportster 1200 Nightster not only a valuable motorcycle but also a testament to Harley’s to push boundaries while remaining true to their roots.