13 Classic Cars Driven by Hollywood Stars

The Hollywood glitz and glamour are incomplete without the coolest cars the world has ever seen. With luxury and style reigning supreme, classic cars have always stood out as a symbol of status, elegance, and a touch of nostalgia among the litany of million-dollar Lamborghinis, Ferraris, and Maybachs.

Many Hollywood stars have been charmed by vintage automobiles since the golden age of modern cinema. Same way they carefully choose their red carpet rides, classics can be more than just a mode of transportation – the representatives of an era and an extension of the stars themselves.

Ladies and gentlemen, join us in this scenic drive through Beverly Hills, Bel Air, Malibu, Santa Monica, Pacific Palisades, Hollywood Hills, and wherever else these legendary figures love to frolic, as we raise our glasses to the iconic classic cars that captured the hearts of some of Hollywood’s finest performers — who made us laugh, cry, and dream.

Steve McQueen – 1968 Ford Mustang GT 390 (“Bullitt”)

Both Steve McQueen and the 1968 Ford Mustang fastback owe a good chunk of their fame to the Peter Yates-directed classic “Bullitt” movie released the same year. In fact, McQueen and his Bullitt made the ‘68 GT 390 Mustang one of the most iconic cars in film history.

The car chase scene with McQueen behind the wheel of a Highland Green Mustang proved to be the benchmark and one of the most influential car chase sequences in the history of the Big Screen.

It’s rather unfortunate that McQueen couldn’t buy the car after filming. The Bullitt Mustang changed hands several times over the years until resurfacing in a barn in 2018. In 2020, it fetched $3.74 million at a Florida auction to become one of the most valuable Mustangs ever sold.

James Dean – 1955 Porsche 550 Spyder (“Little Bastard”)

Actor James Dean bought the 1955 Porsche 550 Spyder in 1955 and gave it the nickname “Little Bastard,” although some accounts have it that custom painter Dean Jeffries was actually behind the nickname, which he painted on the car’s rear deck along with James’ racing number ‘130.’ In any case, “Little Bastard” captured the actor’s adventurous personality.

Known for his love of fast cars and racing, James acquired the 550 Spyder just as he got more involved in motorsport. He had it customized by famous Hollywood modder George Barris. Sadly, James died in a fatal collision with another vehicle at the junction of Highways 46 and 41 near Cholame, California. He was just 24.

The Little Bastard became even more of a legend following reports that other cars that used parts salvaged from the accident encountered various accidents and mishaps. The car itself disappeared under mysterious circumstances in the 1960s.

Paul Newman – 1979 Datsun 280ZX

The late Hollywood actor and director Paul Newman enjoyed a distinguished career as a racing driver, further embellishing his involvement with the Datsun brand (now Nissan). He became involved with the Japanese marque as a professional driver and later a racing team owner during the late 1970s and early ‘80s.

Newman raced the 280ZX to numerous successes in the SCCA (Sports Car Club of America) series. He competed in prestigious events such as the 24 Hours of Le Mans. The 1979 Datsun 280ZX featured a 2.8-liter inline-six engine that produced 135 horsepower and achieved 120 mph top speed in stock form. Paul’s versions were extensively modified for racing.

Marilyn Monroe – 1956 Ford Thunderbird

Marilyn Monroe’s 1956 Ford Thunderbird is widely considered a perfect representation of 1950s Hollywood glamour. The actress’s apparent love for the car helped transform it into a symbol of sophistication and glamour, especially following her marriage to playwright Arthur Miller and the numerous photographs depicting the couple and their beloved Thunderbird.

She reportedly got it as a gift from business partner and friend Milton Greene. The 1956 Thunderbird featured a 215 to 225-hp 312 cu-in V8 engine mated to a 3-speed manual or a Ford-O-Matic automatic transmission.

Clark Gable – 1935 Duesenberg Model JN

Duesenberg’s Model JN flaunted a luxurious interior, as was the marque’s hallmark. The American marquee was known for high performance, luxury, and craftsmanship, which was evident in the Model JN’s leather upholstery, intricate woodwork, and advanced (for the time) instrumentation.

Founded by brothers August and Fredrick Duesenberg, the Indiana-based automobile company produced cars between 1913 and 1937. The Model JN was one of the company’s final models and was often customized to owner specifications.

Clark Gable was one of Hollywood’s hot shots back then, making his acquisition of the 1935 Duesenberg Model JN in 1956 feel like the most natural thing in the world.

Elvis Presley – 1955 Cadillac Fleetwood Series 60

As one of the most influential cultural icons in the history of popular music, Elvis Presley’s 1955 Cadillac Fleetwood Series 60 shares his fame just for being associated with the King of Rock ‘n’ Roll. Elvis bought the pink Cadillac in early 1955, just as his career was starting to pick up.

Consequently, Elvis came to love the Fleetwood the way Miss Monroe loved her Thunderbird. The car racked up many miles through music tours and daily driving, symbolizing the star’s burgeoning success. The iconic Cadillac wasn’t always pink, though.

It was blue before Elvis had it repainted the now-famous pink shade. Bruce Springsteen talked about it in his “Pink Cadillac” song. It’s still on display at the Memphis Graceland Museum.

Paul Walker – 1994 Toyota Supra (From “The Fast and the Furious”)

Although Paul Walker did not personally buy or own the classic Supra featured in the “Fast and Furious” film franchise, the actor’s portrayal of Brian O’Conner and his 1994 Toyota Supra greatly boosted each other’s status as a beloved figure in car culture.

The movie effectively transformed both the two-legged and four-wheeled stars into legends among enthusiast communities, highlighting the intersection of Hollywood, car culture, and personal legacy.

This car verifiably rekindled America’s interest in Japanese sports cars and the tunings that go with it. The Supra that Walker drove in the movie fetched $550,000 at auction in 2021.

Sean Connery – 1964 Aston Martin DB5 (From “Goldfinger”)

It’s hard to imagine a James Bond film without a James Bond car, all thanks to Sean Connery and his prized 1964 Aston Martin DB5 in the “Goldfinger” movie. Goldfinger was neither the first James Bond film nor the first to feature notable cars.

The same Sean Connery drove a 1961 Sunbeam Alpine Series II in the first James Bond film, “Dr. No,” as well as a 1935 Bentley 4.5 Liter in the second one, but neither of the two were as iconic or even as recognized in the film and auto industry as the DB5.

As Dr. No introduced Sean as James Bond and set the stage for the long-running spy series, the Aston Martin DB5 effectively introduced the “James Bond Car” phenomenon. They say it’s the most famous car in the world.

Frank Sinatra – 1955 Continental Mark II

The Continental Mark II was the first fruit of the newly established Continental Division Ford Motor Company luxury brand. It was a hand-built luxury car positioned above Lincoln and intended to revive the prestigious Continental nameplate originally associated with the Lincoln brand.

The Mark II could stare down Rolls-Royce, Cadillac, and the most luxurious cars in the world.  Boasting around $10,000 (approximately $114,000 in today’s money) price tag, the Continental Mark II was one of the most expensive American cars of its time.

The company built just some 3,000 units, one of which was acquired by a man known for his refined taste and love of luxury, legendary singer and actor Frank Sinatra.

Jay Leno – 1955 Mercedes-Benz 300SL Gullwing

James Douglas Muir Leno (popular as Jay Leno) is just as famous for his massive $50 million car collections as his “TV host” personality. With over 181 automobiles (excluding over a hundred motorcycles) in the man’s garage, settling for just one car is difficult. If the man has named a single car as his absolute favorite in his collection, we’re yet to hear about it.

However,  in various interviews and videos, Mr. Leno has expressed a remarkable fondness for a few cars, especially the 1955 Mercedes-Benz 300SL Gullwing. The comedian, TV host, and car enthusiast often praised the car’s design, engineering, and driving experience.

Jerry Seinfeld – 1964 Porsche 911

The classic 1964 911 is a significant part of the Jerry Seinfeld’s extensive car collection. The man and Porsche — especially Vintage Porsches — are like five and six, but the ‘64 Porsche 911 has a special place in his collection, a cherished piece of automotive history.

He often references these cars in his shows and television projects. The 1964 Porsche 911 was born with an air-cooled, rear-mounted 2.0-liter flat-six engine mated to a 5-speed manual transmission, producing around 130 horsepower in its original configuration.

Rita Hayworth – 1953 Cadillac Series 62 Ghia

Marilyn Monroe was not the only actress who contributed to the ’50s Hollywood glamour by taking possession of a sleek, nicely built automobile. Her 1953 Cadillac Series 62 Ghia was a limited-production, custom-built car designed by the Italian coachbuilder Ghia and reserved for select clients such as celebs and dignitaries.

No two Series 62 Ghias were exactly the same, as the car featured a bespoke design tailored to the customer’s taste. However, the car’s overall design represented a combination of Italian styling and American luxury, complete with fine leather upholstery, plush carpeting, and elegant wood trim.

Clint Eastwood – 1975 Ferrari 365 GT4 BB

The Ferrari BB is enshrined in Ferrari’s automotive history, just like Clint Eastwood in the Hollywood industry. The car was the Prancing Horse’s first-ever mid-engined road car, departing from the Italian marque’s traditional front-engine layout.

Clint Eastwood’s 1975 Ferrari 365 GT4 BB is one of the world’s rarest classic cars, with an estimated 387 examples produced in its entire three-year production run spanning 1973 to 1976. Placing the engine behind the driver and passenger seats improved the car’s weight distribution and handling.

It used a 4.4-liter flat-12 engine with around 340 horsepower and the ability to urge the car to 60 mph in 5.4 mph.  seconds. Thus, BB was one of the world’s fastest cars at the time, with a top speed of around 174 mph.