8 Top Harley-Davidson Softails of All Time

Harley-Davidson stands as one of the oldest motorcycle manufacturers still in operation today. Established in 1903 from a small shed in Milwaukee, Wisconsin, Harley is known for its staunch traditions and distinctive styles, often stirring debate among enthusiasts. Over the past 120 years, the brand has significantly influenced the perception of motorcycling, producing both remarkable and, admittedly, less-than-stellar motorcycles.

With a legacy nearly as extensive as the automobile industry, Harley-Davidson has had its share of highs and lows. Despite critiques of being stuck in the past, the company has consistently worked to innovate and enhance its engines through the years. Though there have been failures, there have also been remarkable triumphs.

One of these successful narratives began in 1984. Just three years before, Harley-Davidson had been reacquired from American Machine and Foundry (AMF). Faced with reputation issues due to poor quality, the new ownership aimed to reclaim some of Harley’s former glory.

The Harley-Davidson Softail debuted in 1984 as one of the first models featuring the Evolution engine. Drawing inspiration from the home customization trend popularized in the 1970s, the initial Softail combined nostalgic aesthetics with a forward-looking approach. In honor of more than four decades of Harley history, we delve into some of the finest Harley-Davidson Softails ever produced.

What is a Softail?

The trend of motorcycle customization exploded after World War II, hitting its peak during the 1970s and 1980s. Enthusiasts, both amateur and professional, transformed factory bikes into unique rolling art pieces. The term “chopper,” referring to motorcycles with elongated front ends, gained popularity, especially through films like 1969’s Easy Rider.

Choppers typically utilized rigid frames, which were humorously termed “kidney busters” due to their lack of rear suspension. While visually striking, such hardtail motorcycles were not known for comfort.

Fresh from the AMF era and equipped with one of the finest Harley-Davidson engines ever, the Evolution, Harley sought to exploit the hardtail aesthetic and the chopper craze with the introduction of the Softail.

The original Softail, released for the 1984 model year, had a secret advantage: a cantilever rear suspension cleverly hidden beneath the seat. This innovation offered a smoother ride while maintaining the classic hardtail appearance.

The combination of the Softail’s distinctive styling and the dependable Evolution engine made for an instant hit. It seamlessly offered retro charm alongside modern reliability and comfort, serving as a customizable chopper for riders looking to personalize or savor it right off the showroom floor.

Over the past 40 years, Harley has leveraged the Softail design to create some of the most cherished and aesthetically pleasing motorcycles of all time.

[Featured image by Rooster via Wikimedia Commons | Cropped and scaled | CC BY-SA 3.0]

Fat Boy

First introduced for the 1990 model year, the Fat Boy is celebrated for its simple yet elegant styling and cruiser-friendly design. Recognized as one of the top Harley-Davidsons in history, the Fat Boy remains in production as of 2024.

Willie G. Davidson, part of the Davidson family, played a crucial role in the AMF buyback process in 1981. With the company on the mend and steadily restoring its reputation, he embarked on a personal project during the late 1980s. Collaborating with designer Louie Netz, Davidson demanded rigorous testing to ensure the Fat Boy met high standards before its public debut, even personally riding it to Daytona in 1988 and 1989.

Alongside its iconic Softail rear end, the Fat Boy was a muscle cruiser powered by an 82 cubic inch (1,337 cc) 45-degree V-twin engine, producing 67 horsepower at 6000 RPM. The following year, the 1991 model gained fame when it appeared in Terminator 2, featured in a scene with Arnold Schwarzenegger. While the real motorcycle likely wouldn’t survive the stunts depicted, it proved to be a durable and popular model.

The Fat Boy evolved over the years. Initially named for its wide frame, the 2024 model has fully embraced its moniker. Featuring a robust 114 cubic inch (1,868 cc) Milwaukee-Eight engine generating approximately 94 horsepower at 4,750 RPM, it preserves the original’s timeless charm while adapting to modern standards.

Heritage Classic

Given the extensive history of Harley-Davidson, heritage plays a significant role in its marketing efforts. The Softail Heritage Classic highlights this legacy, integrating classic motorcycle design elements with modern performance and comfort.

Initially, the original Softail FXST served as a convenient commuter bike, while the Heritage variant was designed as a lightweight bagger. The original model may seem basic by today’s standards, but it has seen numerous enhancements over the years. Like the Fat Boy, the Heritage has maintained ongoing production, including a 2024 version outfitted with the 114 cubic inch Milwaukee Eight engine, representing the pinnacle of Harley’s modern offerings.

Far from being a relic, the Heritage Softail Classic pays tribute to the bikes of yesteryear but features modern amenities in its 2024 model. Unlike its leather-clad predecessors, the Heritage Softail comes equipped with modern essentials such as ABS, a detachable windscreen, LED lights, and a powerful engine delivering 94 horsepower, merging the best of both worlds for today’s riders.

With its classic design and contemporary features, the Heritage Softail Classic remains a favorite among Harley lovers, perfect for weekend adventures or extended journeys. Its lasting appeal and status within the Harley lineup make it one of the finest Softails ever produced.

Crossbones

Harley-Davidsons are synonymous with shiny chrome, but the brand took a different direction in the mid-2000s with the introduction of the Dark Custom line. The Crossbones—unveiled in 2008—showcases this unique design philosophy.

As the flagship of the Dark Custom collection, the Crossbones featured bobber-inspired design elements with dark paint schemes accented by minimal chrome. This model embraced an outlaw aesthetic, boasting a Jolly Roger design on the oil tank alongside a black powder-coated powertrain. With its sprung solo seat and springer front end, it attracted riders craving a distinctive look—whether they were lone stars or everyday commuters. Even years after its production ended, it continues to turn heads.

Powered by a 96B V-twin engine with a displacement of 1,584 cc, the Crossbones produced approximately 94 lb-ft of torque at 3,000 RPM. While horsepower figures are scarce, the bike’s low-end power pays homage to the custom motorcycles that inspired its design.

Unfortunately, the Crossbones did not remain in production for long. Discontinued in 2012 due to changing consumer preferences and declining sales, it nonetheless earns a spot on our list for its gritty rebellion, compelling aesthetics, and raw street presence.

2006 to 2009 Night Train

The Softail Night Train, which debuted in 1998, was an early proponent of the dark aesthetic, powered by the infamous Twin Cam 88 engine. This model featured plastic cam chain tensioners which, in many cases, led to catastrophic engine failures. While some owners experienced minimal issues, those interested in the Night Train should focus on the 2006 to 2009 production years which showcased the enhanced 96 Twin Cam engine.

The Night Train presented an all-black powertrain aimed at showcasing Harley’s custom motorcycling to the European market. More affordable relative to other models, it boasted a custom aesthetic with clean lines, drag bars, and a balance of black powder coating and chrome.

Producing 63 horsepower, it wasn’t the most powerful option, but it excelled in delivering a minimalist experience. Its elongated, low profile caught the eye, even though its weight surpassed 650 pounds. Equipped with a single disc front and rear braking system, the Night Train wasn’t designed for aggressive handling but effortlessly drew attention on city streets with its unique design and deep exhaust note.

[Featured image by John Schanlaub via Wikimedia Commons | Cropped and scaled | CC BY-SA 4.0]

Breakout

The Breakout, a quintessential muscle cruiser reflecting Harley’s distinct style, made its debut in 2013. Its Twin Cam 103 cubic inch (1,690 cc) engine paired with a six-speed transmission showcases a unique mix of power and aesthetics. The low profile and extended rake at the front yield a factory-chopper vibe.

The mutual admiration between Harley-Davidson and muscle cars stems from shared qualities: robust, sparse engines, abundant torque, and a stance that conveys predatory readiness. The Breakout exemplifies these traits effectively.

Harley provided a broad spectrum of customization options for the Breakout, producing a vibrant secondhand market filled with unique motorcycles. With a hefty 240 mm rear tire delivering immense torque, the Breakout is an unabashed muscle bike with striking style.

Harley continuously enhanced the Breakout from 2013 until 2020, when it temporarily exited the American market. By that time, the CVO edition boasted a 110 ci Screamin’ Eagle Twin Cam engine, generating 122 lb-ft of torque at 3,500 RPM.

The Breakout returned stateside equipped with a new Milwaukee Eight 117 ci engine, marking it as only the third Softail model to feature this powerhouse alongside the Low Rider S and Low Rider ST. The Breakout is available as a 2024 model, making it possible to acquire a brand-new one today.

[Featured image by Lothar Spurzem via Wikimedia Commons | Cropped and scaled | CC BY-SA 2.0 DE]

2018 onward Street Bob

The Street Bob represents a nod to Heritage styling in a minimalist package. Since its introduction in 2006, it has been part of the Dyna family, easily recognizable by its visible rear suspension springs. However, after Harley-Davidson discontinued the Dyna line in 2017, the Street Bob transitioned into the Softail family.

Remaining true to its minimalist roots while incorporating modern comforts, the Street Bob became one of the most celebrated models from the Dyna lineup. When it made its Softail debut in 2018, the bike featured the Milwaukee Eight engine in a 107 cubic-inch format, but Harley has since increased its displacement. As of 2024, the Street Bob has upgraded to a 114 cubic-inch engine.

Weighing only 655 pounds, the Street Bob provides a thrilling ride, delivering 94 horsepower and 119 lb-ft of torque. While optional ABS can enhance braking safety, it isn’t standard. Riders seeking the ultimate in long-distance comfort might prefer a Heritage model; the Street Bob embodies the essence of a bobber-inspired street bike.

By focusing on eliminating non-essential components, Harley ensures that the Street Bob offers an unadulterated riding experience, fulfilling all the primary functions of a motorcycle without distractions.

Hydra-Glide Revival

For ardent fans of classic Harley designs, the 75th-anniversary Hydra-Glide Revival is a sight to behold. If you’re attracted to Heritage Classics or vintage Springer Softails, the Revival, replete with unique features, is a must-see.

In 2021, Harley-Davidson initiated the Icons line to pay homage to its illustrious history and iconic motorcycles. The Hydra-Glide Revival serves as the newest flagship of this series, capturing the charm of the 1950s-era Hydra-Glides—most notably the 1956 FLH—while integrating advanced modern amenities.

Although it sports a vintage aesthetic with features such as whitewall tires, a raised solo seat, and a classic paint job, the Hydra-Glide Revival is anything but antiquated. The ’50s motor’s 74 cubic-inch displacement has been updated to the contemporary Milwaukee Eight 114 cubic-inch V-twin, and enhancements abound.

Beyond boasting a modern suspension that significantly surpasses the vintage FLH, this edition delivers an impressive 94 hp and 119 lb-ft of torque, ensuring it excels whether cruising city streets or embarking on extended road trips.

Every aspect of the limited-run Hydra-Glide Revival serves as a tribute to the golden age of Harley, encapsulated in a modernized format. It stands as a premium offering for true Harley enthusiasts.

Softail Standard

Harley is not typically associated with affordability, and as motorcycle specs escalate, prices often follow suit. The Softail Standard represents the most economical entry point into the Softail family. With its understated design and classic Softail aesthetics, this model offers just what riders need to enjoy the open road.

Available in limited color choices of Vivid Black or Billiard Gray, the Softail Standard reflects Harley’s ambitions of marrying simplicity with performance. Featuring a Milwaukee-Eight 107 cubic inch engine, mid-mount foot controls, a low seat height, and a manageable weight, the Softail Standard represents a versatile choice for any rider.

Serving as a nod to the original 1984 Softail vision, the Standard embodies a classic rigid frame, an unembellished charm, and iconic Harley styling, making it an attractive option for anyone wishing to join the Harley community. At a price of $14,999, it may not be the most affordable in comparison to sport-cruisers, but it certainly maintains its worth within the Harley hierarchy.

No matter if the Softail Standard speaks to you or if another model captures your heart, rest assured that Harley has been crafting these bikes since 1984, with no indications of stopping in sight.