10 Of The Most Expensive Custom Harley-Davidson Motorcycles Ever Sold

What makes a motorcycle worth more than a house? For Harley-Davidson enthusiasts, it's about more than just the ride — it's the legacy, the story, and the craftsmanship. Since its founding in 1903 in Milwaukee, Wisconsin, Harley-Davidson has become a symbol of freedom, rebellion, and the open road.

While all of the best Harley-Davidsons have a place in the American motorcycling tradition, custom Harleys often represent a specific part of American cultural history. Imagine a Harley encrusted with diamonds, or one that rolled off the set of "Easy Rider" and into the hearts of millions. There are even machines that once belonged to Elvis Presley and Pope Francis. Some of these machines are living reminders of motorcycling history, while others push the limits of what a motorcycle can be.

In this article, we'll journey through the incredible world of custom Harley-Davidson motorcycles that shattered auction records to reveal why collectors and enthusiasts are willing to pay such eye-watering amounts. Let's see what makes these motorcycles so valuable and uncover the stories behind their sky-high prices.

In 2010, artist Jack Armstrong unveiled the Cosmic Starship, an extraordinary blend of art and engineering. Armstrong, known for his Cosmic Extensionalism style, transformed a 2009 Harley-Davidson V-Rod with acrylic paints and 37 layers of clear coat, creating a design that bursts with vibrant colors and abstract patterns. The result was a motorcycle as much at home in an art gallery as on the open road.

The bike debuted at Bartels' Harley-Davidson dealership in Marina Del Rey, where Lorenzo Lamas rode it down a red carpet after it was dramatically lowered from the air. This grand unveiling emphasized its dual identity as a high-performance machine and a work of fine art. In 2012, the Cosmic Starship Harley sold for $3 million, securing its place as one of the most expensive motorcycles ever.

Beneath its dazzling exterior, this classic Harley is powered by a Revolution V-twin engine with a liquid-cooled 1130cc capacity, ensuring it performs as impressively as it looks. The Cosmic Starship Harley is a masterful fusion of mechanical craftsmanship and artistic vision that is coveted by collectors and enthusiasts alike.

The Harley-Davidson Bucherer Blue Edition is a jaw-dropping machine that was born from a collaboration between Harley-Davidson and the Swiss luxury watchmaker Bucherer Carl. The Bucherer Blue Edition is unlike any motorcycle ever made in the sense that its handcrafted frame took over 2,500 hours to build, and every component is plated in silver before being coated with a deep blue hue.

One of its standout engineering feats is the transparent engine housing, allowing admirers to view the engine in motion—an exceptionally rare design choice. Another innovation is the seamless integration of a bespoke Carl F. Bucherer watch into the fuel tank, encased beneath an armored glass dome. The luxury doesn't stop there — this Harley boasts over 360 diamonds, gold-plated screws, and fine cowhide leather accents. Every detail screams exclusivity and craftsmanship.

This stunning motorcycle debuted with a price tag of just under $2 million, cementing its position as one of the most expensive Harley-Davidsons ever crafted.

Few motorcycles have achieved the legendary status of Peter Fonda's "Easy Rider" Chopper, which is also known as Captain America. This Harley-Davidson panhead became an enduring symbol of freedom and rebellion, capturing the spirit of 1960s counterculture like no other machine.

Designed by Cliff Vaughs and Ben Hardy, this custom chopper featured a stretched-out front fork, a rigid frame, and an unmistakable red, white, and blue paint job representing the American dream. The bike was used extensively in the film, ridden by Fonda as he and Dennis Hopper's characters embarked on a road trip across America. Its iconic status cemented its place in motorcycle history, making it a cultural touchstone.

The original Easy Rider chopper faced a rocky history, with most of the bikes used in the film either stolen or destroyed. However, one surviving model restored by Dan Haggerty was auctioned in 2014. This piece of cinematic history fetched an astonishing $1.35 million, reflecting its enduring appeal to both motorcycle enthusiasts and film buffs alike.

Not all motorcycles are built to turn heads with flashy designs or celebrity connections. Some carry their value in their history, and the 1908 Harley-Davidson Strap Tank is one such motorcycle. As one of the oldest surviving Harley-Davidson models, this motorcycle is a relic of the company's early years, representing the pioneering spirit that launched the brand into worldwide recognition.

This particular model, discovered in 1941 by David Uihlein in a barn near Milwaukee, is a time capsule of motorcycling history. Uihlein kept the bike in Wisconsin for 66 years, preserving it as a nearly untouched relic of Harley-Davidson's infancy. Remarkably, this bike boasts its original tank, wheels, engine belt pulley, seat cover, and muffler sleeve, making it one of the most authentic examples of its kind.

The 1908 Strap Tank gets its name from the nickel-plated steel straps that hold its fuel and oil tanks in place. It's a visual callback to an era when motorcycles were little more than motorized bicycles, and engineering innovation was just beginning to take shape. In January 2023, this pristine example of Harley-Davidson's early craftsmanship fetched a record-breaking $935,000 at a Mecum Auctions event.

What happens when the King of Rock and Roll meets the king of the road? You get Elvis Presley's 1976 Harley-Davidson FLH 1200 Electra Glide, a motorcycle as legendary as its owner. Purchased in August 1976, this limited-edition Electra Glide was designed as a bicentennial model to celebrate 200 years of American independence by featuring a distinctive blue-and-black color scheme that made it an instant collector's item. 

Elvis registered the bike to his Palm Springs home before shipping it to Graceland. However, it saw minimal use and was put up for auction with just 126 miles on the odometer –a testament to its near-mint condition. In early 1977 — only three months before his passing — Elvis sold the motorcycle back to a local dealership, adding another layer of intrigue to its history.

After leaving Elvis' hands, the bike spent decades on display, first at a New Jersey hotel and later at the Pioneer Auto Museum in South Dakota, where it remained for over 36 years. In 2019, this extraordinary 1976 Harley-Davidson motorcycle went up for auction and fetched a staggering $800,000, making it one of the most expensive Harley-Davidsons ever sold. Its sale included the original title — complete with Elvis' signature — and keys.

It's not every day that a motorcycle becomes a star-studded icon, but the 2001 Harley-Davidson Dyna Super Glide did just that. This Harley was once owned by Jay Leno and signed by a host of A-list celebrities, making it a pop culture artifact. This bike was auctioned to benefit the Twin Towers Fund after the tragic events of 9/11, cementing its place in history as more than just a regular Harley motorcycle. 

The bike appeared on "The Tonight Show" for 30 days, where Jay Leno rallied an impressive roster of celebrities to autograph it. The star-studded list includes Tom Cruise, Sylvester Stallone, Arnold Schwarzenegger, Samuel L. Jackson, Nicole Kidman, John Travolta, and many more. With 248 miles on the odometer, this Harley stands in near-mint condition, making it a collector's dream. This motorcycle was later sold for an auction price of $360,200.

Underneath its celebrity signatures and black exterior, the Dyna Super Glide boasts a 1449cc V-Twin engine paired with a 5-speed manual transmission. Its low-profile suspension, raked-out front fork, and low-slung custom seat with a tapered passenger pillion ensure it's as stylish as it is functional. Easy-reach handlebars and foot controls add to the comfortable yet striking design.

This 2013 Harley-Davidson FXD Dyna Super Glide gifted to Pope Francis is anything but ordinary. Presented to the pontiff during Harley-Davidson's 110th anniversary celebration, this motorcycle is an unexpected intersection of faith, charity, and craftsmanship.

What makes this Harley truly remarkable is its unique provenance. Bearing Pope Francis' signature, Francesco, inscribed onto the fuel tank, the bike instantly became a collector's dream. Despite its immaculate condition, this Harley wasn't destined for the open road. Instead, it served as a symbol of goodwill that embodied the charitable spirit of its owner.

In February 2014, this unique Harley was auctioned by Bonhams in Paris. Pope Francis' Harley fetched an impressive $327,000. Proceeds from the sale were donated to Caritas Roma, a charity supporting the renovation of a soup kitchen and hostel in Rome — a gesture aligned perfectly with Pope Francis' commitment to helping those in need.

When it comes to rock 'n' roll legends, few names shine brighter than Jerry Lee Lewis, and his 1959 Harley-Davidson FLH Duo-Glide is as iconic as the man himself. Lewis was known for his electrifying performances and rebellious spirit, qualities that perfectly matched the Harley-Davidson brand.

The 1959 FLH Duo-Glide marked a major leap forward for Harley-Davidson, being the first model to feature rear hydraulic suspension. This innovation gave the bike its "Duo-Glide" nickname, offering riders an unprecedented level of comfort and stability compared to the rigid-frame designs of earlier models. At its heart was the 74 cubic-inch Panhead engine, delivering a combination of power and reliability that became synonymous with Harley-Davidson's legacy.

What set this motorcycle apart wasn't just its technical prowess but its personal touches. Jerry Lee Lewis was known for customizing his possessions, and his Harley-Davidson FLH was no exception. In 2015, this 1959 Harley-Davidson went up for auction at a Mecum event, where it fetched an impressive $385,000, making it one of the most expensive Harleys ever sold.

The Harley-Davidson 8-Valve Racer's speed, power, and innovation made it a crown jewel of Harley-Davidson's early racing years. Originally built in the 1910s and 1920s for board track racing, this motorcycle wasn't designed for casual riders — it was a machine made to dominate the track.

The 8-Valve Racer's standout feature was its groundbreaking engine, which boasted eight overhead valves for superior airflow and combustion efficiency. This innovation allowed the bike to reach speeds of more than 100 mph, a jaw-dropping feat for its time. Built for extreme performance, the racer featured a lightweight frame, minimal bodywork, and no brakes, showcasing Harley-Davidson's single-minded focus on speed and agility.

These bikes were not mass-produced, making surviving models incredibly rare and valuable. In 2015, a pristine 1927 FHA 8-Valve Racer sold for $600,000 at auction, underlining its status as a highly sought-after collector's piece. Its unparalleled engineering and historical significance make it a true crown jewel for collectors.

Few motorcycles in cinematic history are as iconic as the 1991 Harley-Davidson FLSTF Fat Boy, immortalized by Arnold Schwarzenegger in "Terminator 2: Judgment Day." This bike became an instant legend after its memorable debut in the film, when a leather-clad Schwarzenegger drove one away from a bar fight as the unstoppable Terminator. The motorcycle's commanding design, paired with Schwarzenegger's towering presence, elevated the gripping chase scenes in the film to unforgettable heights.

This particular bike wasn't just a prop, as it was carefully customized to handle the rigors of Hollywood action sequences. Modified exhaust and valve tweaks ensured it could handle jumps and tight turns with ease. Beyond that, its low-slung design, wide tires, and solid disc wheels — along with the added red trim and shotgun holster — made it the perfect choice for a character who was as unrelenting as the machine he rode. Today, this motorcycle holds a revered status among both Harley-Davidson fans and movie buffs.

All of this helped the original "Terminator 2: Judgement Day" Fat Boy sold at auction in 2018 for an eye-watering $480,000.