Behind the steely gaze of Hollywood legend Clint Eastwood lies a passion few know about—a collection of automotive masterpieces that would make any enthusiast weak at the knees. These aren’t just cars; they’re rolling art, mechanical time capsules representing the pinnacle of their eras.
From pre-war European elegance to raw American muscle, Eastwood’s garage houses vehicles so rare that museums compete for the chance to display them. Each carries a story as compelling as any film he’s directed.
As we explore these ten remarkable machines, we glimpse not just automotive history, but also the sophisticated taste of a cultural icon whose appreciation for craftsmanship extends far beyond the silver screen.
1. 1937 Bugatti Type 57SC Atalante
This rare automotive jewel stands as a testament to French engineering excellence. Jean Bugatti’s masterful design combines art deco influences with racing heritage, creating a silhouette that remains breathtaking even today. Under its elegant hood sits a 3.3-liter straight-eight engine producing 170 horsepower – impressive for its era.
Hand-crafted aluminum bodywork flows over the chassis in graceful curves, while the signature horseshoe grille announces its prestigious lineage. Fewer than 40 examples were ever built, making its presence in Eastwood’s collection particularly notable.
The supercharged variant delivers thrilling acceleration and a top speed approaching 120 mph, remarkable for the 1930s. Its cabin features luxurious leather upholstery and intricate instrumentation panels showcasing the finest craftsmanship of its time. Automotive historians universally acknowledge this model as one of the most significant pre-war sports cars ever created.
Each surviving example now commands multi-million dollar valuations at auction, reflecting both its historical importance and enduring beauty.
2. 1955 Mercedes-Benz 300SL Gullwing
Automotive history changed forever when Mercedes unveiled this revolutionary sports car. Those dramatic upward-opening doors weren’t merely for show – they solved a practical problem created by the car’s innovative space-frame chassis.
Beneath its sensuous bodywork, the 300SL houses a 3.0-liter straight-six engine tilted at a 45-degree angle to maintain a low hood profile. With 215 horsepower delivered through mechanical fuel injection (a first for production cars), it could reach 160 mph, making it the fastest production car of its time.
The interior blends sporting functionality with luxury appointments, featuring plaid cloth seats and a large steering wheel necessary for managing its somewhat heavy steering. Production numbers remained limited with just 1,400 coupes manufactured between 1954 and 1957.
The distinctive “eyebrows” above the wheel arches enhance both appearance and aerodynamics. Famous owners have included Pablo Picasso, Sophia Loren, and Clark Gable, placing Eastwood in prestigious company. Today, these automotive icons routinely sell for seven-figure sums.
3. 1936 Cord 810 Westchester
Revolutionary thinking defines this American classic in Eastwood’s garage. Gordon Buehrig’s design broke nearly every convention of 1930s automobiles with its lack of running boards, hidden headlights, and coffin-nose front end lacking a traditional grille.
Technological innovation appears throughout – front-wheel drive allows for a lower profile, while the “coffin-nose” hood houses a V8 engine lying backward in the chassis. The dashboard resembles an aircraft cockpit, featuring engine-turned metal and elegant instrumentation. Four-speed pre-selector transmissions allow drivers to choose gears with a finger touch before engaging the clutch.
Cord’s disappearance from the market after just two years of production has only enhanced collector interest. The car’s streamlined appearance influenced automotive design for decades to come. A total of 1,174 units were produced in the first year, making surviving examples extraordinarily valuable.
Eastwood’s specimen represents American engineering ingenuity during an era when boundaries were meant to be pushed. The clean lines and art deco influences ensure this vehicle remains as visually striking today as when it first shocked the automotive world nearly nine decades ago.
4. 1963 Ferrari 250 GT Lusso
Ferrari created automotive art with this grand touring masterpiece. Designed by Pininfarina and bodied by Scaglietti, the Lusso (Italian for “luxury”) represents perhaps the most beautiful expression of Ferrari’s classic 250 series. Its 3.0-liter V12 engine produces 240 horsepower, delivering the perfect balance between performance and refinement.
The sweeping greenhouse and fastback profile create a silhouette that has influenced sports car design for generations. From the delicate egg-crate grille to the slightly kicked-up tail, every aspect of its bodywork exhibits flawless proportions. Inside, a unique dashboard layout positions all gauges in the center of the dash, allowing the steering wheel to sit lower for better visibility.
The cabin combines leather, wood, and aluminum in a driver-focused environment that remains comfortable for long-distance travel. Ferrari built just 350 examples between 1962 and 1964, making this a particularly coveted addition to Eastwood’s collection.
Famous Lusso owners include Steve McQueen, whose example sold for nearly $3 million in 2007. The harmonious design and superb driving dynamics make this Ferrari among the most celebrated grand touring cars ever created.
5. 1965 Shelby Cobra 427
Raw American muscle defines this legendary roadster in Eastwood’s possession. Carroll Shelby’s vision resulted in perhaps the most thrilling driving experience ever created – a lightweight British AC Ace body wrapped around a monstrous Ford 427 cubic inch V8 engine. With 425 horsepower propelling less than 2,500 pounds, acceleration borders on violent, reaching 60 mph in just over 4 seconds – faster than many modern supercars.
The wide fenders accommodate massive tires necessary to transfer all that power to the pavement, creating the iconic muscular stance. Minimal creature comforts reflect its focus on performance above all else. The spartan cockpit features basic gauges, a wood-rimmed steering wheel, and little else to distract from the driving experience.
348 examples were built between 1965 and 1967, with true originals commanding astronomical prices today. The tremendous sound from its side pipes remains unforgettable for anyone lucky enough to experience it. Cobras proved devastatingly effective on racetracks worldwide, dominating GT racing throughout the mid-1960s.
This particular model represents the ultimate expression of Shelby’s philosophy: maximum performance through simplicity and overwhelming power.
6. 1947 Chrysler Town and Country Convertible
Among the rarest vehicles of post-war America sits this wooden-bodied beauty in Eastwood’s collection. Chrysler created only 8,368 examples between 1946 and 1948, combining luxury with distinctive styling that married metal and wood in a unique fashion. The exterior features white ash wood framing with mahogany panels, requiring exceptional craftsmanship to maintain even today.
Collectors refer to these models as “woodies,” and maintaining their complex bodywork demands specialized knowledge. Under the hood resides a straight-eight engine producing 135 horsepower, paired with Chrysler’s semi-automatic “Fluid Drive” transmission. Such technology represented cutting-edge automotive engineering for its era.
The spacious interior boasts plush upholstery, extensive wood trim, and art deco inspired instrumentation. Its broad grille and prominent hood ornament announce classic American styling cues that defined the immediate post-war period. Restoration costs often exceed the market value of these automobiles, making well-preserved examples particularly valuable.
Front and rear passengers enjoy ample room, reflecting American automotive priorities of the late 1940s. This convertible represents American optimism following World War II, when automotive companies returned to civilian production with renewed vigor and creativity.
7. 1931 Duesenberg Model J
Automotive royalty graces Eastwood’s garage in the form of this magnificent pre-war luxury machine. When introduced, no car in America cost more or offered greater prestige than the Model J. Each chassis alone cost $8,500 in 1931 (equivalent to nearly $160,000 today) before custom coachwork was added. Fred and August Duesenberg engineered a masterpiece around a massive 420 cubic inch straight-eight engine producing 265 horsepower when contemporary Cadillacs offered just 90.
Top speeds reached an astonishing 116 mph, creating the phrase “it’s a Doozy” in American vernacular. Custom bodywork was handled by prestigious coachbuilders like Murphy, Derham, and LeBaron, with no two cars exactly alike. The dashboard features extensive engine-turned aluminum and precisely crafted gauges monitoring every aspect of the powerful engine.
Hydraulic brakes on all four wheels provided stopping power few contemporaries could match. Hollywood legends Gary Cooper, Clark Gable, and Greta Garbo all owned Duesenbergs, establishing the model’s connection to the entertainment elite.
Production ended with approximately 480 chassis built, making surviving examples extraordinarily valuable. Ownership of a Model J represents the pinnacle of classic car collecting.
8. 1958 Porsche 356 Speedster
Automotive purity defines this German sports car standout within Eastwood’s impressive collection. Ferry Porsche created the 356 Speedster specifically for the American market at the suggestion of importer Max Hoffman. Its minimalist approach included a removable windshield, simple bucket seats, and side curtains instead of roll-up windows.
Weighing just 1,670 pounds, the air-cooled flat-four engine needs only 70 horsepower to deliver thrilling performance through mountain roads. Flowing curves hide the Volkswagen Beetle DNA that underpins this early Porsche, though every component was refined for sporting use. Famous owners have included James Dean, Steve McQueen, and Jerry Seinfeld, cementing its status in popular culture.
Production numbers remained low with just 4,144 Speedsters built between 1954 and 1958. Cold weather driving requires serious commitment, as weather protection proves minimal at best. The simple dashboard features just the essential gauges in a purposeful layout.
Enthusiasts particularly prize the final 1958 models with improved suspension and more powerful engines. Values have skyrocketed in recent decades, with exceptional examples commanding over half a million dollars at auction.
9. 1966 Lamborghini 400 GT 2+2
Italian craftsmanship shines through every aspect of this early Lamborghini in Eastwood’s stable. Ferruccio Lamborghini created this grand touring machine after feeling dismissed by Enzo Ferrari when suggesting improvements to his Ferrari. The sophisticated V12 engine was designed by Giotto Bizzarrini, who previously engineered Ferrari’s legendary 250 GTO. With 320 horsepower flowing through an in-house five-speed transmission, the 400 GT delivers both speed and refinement.
The 2+2 designation indicates small rear seats, making this a somewhat practical sports car for its era. Carrozzeria Touring constructed the elegant aluminum bodywork using their superleggera (super light) construction technique. Inside, occupants enjoy handcrafted leather seats, comprehensive instrumentation, and wood trim throughout the cabin.
Only 247 examples were produced between 1966 and 1968, making this among the rarest Lamborghinis ever created. Despite its 150+ mph capabilities, the grand touring focus ensures comfort during long-distance driving. The front-mounted engine layout differs dramatically from later mid-engine Lamborghini supercars.
Automotive historians consider this model crucial in establishing Lamborghini as a legitimate competitor to Ferrari, forever changing the Italian sports car landscape.
10. 1939 Alfa Romeo 8C 2900B
Automotive excellence reaches its pre-war zenith with this extraordinary Italian thoroughbred. Racing technology transferred directly to the road makes this perhaps the most sophisticated automobile of its era. The supercharged straight-eight engine produces 180 horsepower from just 2.9 liters, breathtaking output for 1939.
Carrozzeria Touring created the stunning bodywork, with each example slightly different according to customer specifications. Four-wheel independent suspension and hydraulic brakes provided handling capabilities decades ahead of competitors. Fewer than 40 examples were built in total, with many lost during World War II.
The surviving cars rank among the most valuable automobiles on earth, with recent sales exceeding $20 million. Long hood proportions house the magnificent engine, while the passenger compartment sits far back on the chassis in classic grand touring style.
The interior features handcrafted leather and a purposeful array of instruments monitoring the sophisticated mechanicals. Contemporary road tests praised its 110 mph top speed and exceptional handling balance.
Racing success included overall victory at the 1938 Mille Miglia, Italy’s most prestigious road race. Automotive historians universally acknowledge this model as perhaps the ultimate pre-war sports car, combining beauty, performance, and exclusivity in unprecedented fashion.
