There are the ones we rely on for daily commutes, shuttling kids to school, grabbing groceries, or hauling home improvement supplies. These cars are functional, dependable, practical—and, admittedly, a bit mundane.
And then there are the rare machines that transcend mere transportation. These cars flirt with the realm of artistry, earning acclaim as engineering marvels. They celebrate speed, opulence, and unrestrained creativity—best described as sheer brilliance wrapped in four wheels and rubber.
Throughout the history of motoring, such extraordinary vehicles have always existed. Innovators and visionaries have continually pushed boundaries, asking, “How much faster can we go? How much better can it be?” Every era of automotive history boasts its legends, with names like Bentley, Bugatti, and Ferrari leading the charge.
Many of these icons were produced in extremely limited quantities, and countless examples have been lost to time. However, a fortunate few remain, showcasing groundbreaking performance and craftsmanship from a bygone era.
For those with the means, these cars can become yours. While the average driver balks at spending $100,000 on a car, what compels someone to invest millions in one?
We’ll uncover their fascinating histories, the milestones they achieved, and just how deeply their new owners had to dig into their wallets to secure them.
10. 1962 Ferrari 250 LM
Number produced: 32
Auction price: $6.9 million
By the 1960s, Ferrari recognized a shift in racing from front-engine designs to mid-engine configurations. The result? The Ferrari 250 LM, which featured the 250 Testa Rossa engine mounted mid-car, transforming the company’s 250 P prototype into a competitive GT racer.
Designed by Pininfarina, the 250 LM was envisioned for GT racing. However, the Fédération Internationale de l’Automobile (FIA) doubted Ferrari could meet the 100-unit production requirement for GT-class eligibility.
They were right—Ferrari only built 32 examples. As a result, the 250 LM raced in the prototype class instead, leaving the GT category open for Shelby’s American-built cars to dominate.
Despite this, the 250 LM cemented its place in history with Ferrari’s last victory at Le Mans to date. Its rarity and historical significance make it highly prized among collectors, exemplified when one fetched $6.9 million at auction in 2008.
9. 1965 Shelby Daytona Cobra Coupe
Number produced: 6
Auction price: $7.25 million
The name Shelby Cobra is iconic, but the Shelby Daytona Cobra Coupe carries an equally compelling legacy. This American-made racer was born from a desire to challenge Europe’s dominance in GT racing. In the 1960s, Ferrari reigned supreme in the FIA World Manufacturers Championship GT class. Carroll Shelby set out to dethrone them.
The Daytona Coupe, with its unmistakable blue-and-white livery, packed a snarling 289 cubic-inch Ford V8. It became the first and only American car to defeat Ferrari in a world championship GT race in Europe.
One of only six built, the fourth Daytona Coupe sold at auction in 2009 for $7.25 million—still the highest price ever paid for an American car at public auction.
8. 1904 Rolls-Royce 10 HP
Number produced: 17
Auction price: $7.3 million
In the early days of motoring, 10 horsepower was sufficient to power the humble automobiles of the era. The Rolls-Royce 10 HP, a collaboration between Charles Rolls and Henry Royce, exemplified this. With its 1.8-liter twin-cylinder engine, the car reflected its time—resembling a horse-drawn carriage without the horse.
Of the 17 cars produced, the oldest surviving example, with chassis number 20154, sold for $7.3 million in 2004. This particular model had been updated in the 1930s but was later restored to its original condition in the 1950s. It is a reminder of motoring’s earliest days and a treasured piece of history.
7. 1929 Mercedes-Benz 38/250 SSK
Number produced: 30-35
Auction price: $7.4 million
Short for “Super Sport Kurz” (German for “short”), the SSK was a compact powerhouse designed by Ferdinand Porsche before he founded his eponymous company. Equipped with a 7.1-liter supercharged engine, the SSK was one of the most formidable performance cars of its time.
This particular SSK belonged to English collector George Milligen for over 70 years, maintaining nearly all its original components. Following Milligen’s death, the car sold for $7.4 million in 2004—a testament to its remarkable condition and history.
6. 1937 Bugatti Type 57SC Atalante
Number produced: 11
Auction price: $7.9 million
The Bugatti Type 57SC Atalante is a masterpiece of design and engineering. With its aerodynamic curves, riveted panels, and supercharged 3.3-liter straight-eight engine, it is often heralded as one of the world’s first supercars.
Only 11 Atalantes were produced, and no two were identical. At the Pebble Beach Concours d’Elegance in 2008, one example fetched nearly $8 million, underscoring its status as one of the most coveted classics in existence.
5. 1937 Mercedes-Benz 540K Special Roadster
Number produced: Approximately 25
Auction price: $9.7 million
The 1937 Mercedes-Benz 540K Special Roadster is the epitome of pre-war luxury and performance. Designed by Mercedes-Benz’s in-house coachbuilder, Sindelfingen, the 540K featured a 5.4-liter supercharged straight-eight engine capable of producing 180 horsepower—a staggering figure for the time.
The Special Roadster was an exercise in opulence, with its long hood, flowing fenders, and meticulously crafted details. Only a small number of these cars were produced, each customized to its buyer’s specifications.
One of the most pristine examples of this automotive icon sold at auction in 2012 for $9.7 million. Its combination of rarity, craftsmanship, and historical significance makes it one of the most desirable pre-war cars ever built.
4. 1962 Ferrari 330 TRI/LM
Number produced: 1
Auction price: $9.75 million
The 1962 Ferrari 330 TRI/LM holds a unique place in Ferrari’s history as the last front-engine car to win the 24 Hours of Le Mans. Powered by a 4.0-liter V12 engine producing over 400 horsepower, this one-off prototype was a development of Ferrari’s Testa Rossa series, designed specifically for endurance racing.
The car was driven to victory at Le Mans in 1962 by Phil Hill and Olivier Gendebien, cementing its status as a racing legend. After its retirement from racing, the car changed hands several times before being restored to its original Le Mans configuration.
In 2007, this one-of-a-kind Ferrari fetched $9.75 million at auction, underscoring its historical and technical significance.
3. 1931 Bugatti Type 41 Royale Kellner Coupe
Number produced: 6
Auction price: $9.8 million
The Bugatti Type 41 Royale, often referred to simply as the Royale, was a car fit for royalty—literally. Ettore Bugatti designed the Royale to be the ultimate luxury car, boasting a 12.7-liter straight-eight engine, the largest ever used in a car at the time.
The Royale Kellner Coupe, one of six examples built, was originally intended for European royalty, but the Great Depression stymied Bugatti’s ambitions. This particular car remained in the Bugatti family until it was sold to American collector Briggs Cunningham in the 1950s.
In 1987, the Kellner Coupe sold for $9.8 million, a record-breaking figure at the time. Its grandeur and rarity continue to captivate collectors and automotive historians alike.
2. 1961 Ferrari 250 GT SWB California Spyder
Number produced: 56
Auction price: $10.9 million
The Ferrari 250 GT SWB California Spyder is often considered one of the most beautiful cars ever created. Designed by Pininfarina and built by Scaglietti, the car’s sleek lines and open-top design exude timeless elegance. Under the hood, a 3.0-liter V12 engine delivers both performance and refinement.
This particular example, one of just 56 short-wheelbase versions, gained fame when it was discovered in a French barn in 2014 after being hidden away for decades. Despite its dusty condition, the car was remarkably original and unrestored, which only added to its allure.
In 2015, this “barn find” California Spyder sold for $10.9 million at auction, becoming one of the most valuable classic Ferraris ever sold.
1. 1957 Ferrari 250 Testa Rossa
Number produced: 34
Auction price: $16.4 million
At the top of the list is the 1957 Ferrari 250 Testa Rossa, a car synonymous with motorsport success and design brilliance. Named after the red-painted valve covers of its V12 engine, the Testa Rossa was designed for endurance racing, with a lightweight chassis and a 3.0-liter engine producing over 300 horsepower.
The Testa Rossa won multiple endurance races, including the 24 Hours of Le Mans and the Targa Florio, cementing its reputation as one of Ferrari’s most successful race cars.
In 2011, a pristine example of the 250 Testa Rossa fetched a staggering $16.4 million at auction, setting a new record for the most expensive car ever sold at the time. Its blend of rarity, racing pedigree, and iconic design make it a true masterpiece.
These ten cars represent the pinnacle of automotive history, combining innovation, artistry, and exclusivity. Their staggering prices reflect not only their rarity but also their timeless appeal to collectors and enthusiasts.
As automotive technology continues to evolve, these classic cars remind us of a time when craftsmanship and performance were paramount. Whether you’re a seasoned collector or an aspiring enthusiast, their stories continue to inspire and captivate.
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