11 Legendary Cars Every Man Should Drive Once

October 4, 2025

There’s something about legendary cars that speaks to every man’s sense of adventure and style. These aren’t just vehicles—they’re milestones in automotive history, representing innovation, speed, and timeless design. Getting behind the wheel of a legendary car can be a rite of passage, offering a direct connection to the stories and passions of generations past. Whether you’re a lifelong car enthusiast or just appreciate the thrill of the drive, experiencing these icons is about more than horsepower. It’s about understanding what makes a car truly unforgettable. If you’ve ever dreamed of driving something that stands out in the crowd, this list of legendary cars every man should drive once is for you.

1. Ford Mustang (1965)

The 1965 Ford Mustang isn’t just a car; it’s an American legend. With its long hood, short deck, and unmistakable roar, the original Mustang changed the way people thought about affordable performance. Slip into the driver’s seat, and you’ll feel the raw energy that made the Mustang a symbol of freedom on the open road. The experience is pure and unfiltered—just you, the engine, and the promise of adventure.

2. Porsche 911 (Any Generation)

The Porsche 911 is a masterpiece of engineering that has stood the test of time. Whether you choose a classic air-cooled model or a modern turbocharged variant, the 911 delivers a driving experience that’s both refined and thrilling. The rear-engine layout, precise steering, and iconic silhouette make it one of the most legendary cars every man should drive once. It’s not just about speed—it’s about the way the car connects you to the road.

3. Chevrolet Corvette (C2 Stingray)

The second-generation Corvette, known as the Stingray, took the American sports car to new heights. Its aggressive styling, split rear window (in 1963), and powerful V8 engines made it a force on the street and the track. Driving a C2 Stingray is like stepping into a time machine, where style and performance are in perfect harmony. The sound of that V8 rumbling under the hood is unforgettable.

4. Jaguar E-Type

Often called “the most beautiful car ever made,” the Jaguar E-Type turned heads from the moment it debuted in the 1960s. Its sleek lines and powerful six-cylinder engine make it a true classic. Behind the wheel, you’ll understand why this car captured the hearts of drivers and celebrities alike. The E-Type is a reminder that elegance and excitement can coexist in one legendary package.

5. BMW M3 (E30)

The E30 M3 is the car that put BMW’s M division on the map. Built for racing but civilized enough for daily driving, the E30 M3 offers sharp handling, a high-revving four-cylinder engine, and a chassis that begs to be pushed. For many, it’s the ultimate expression of the “driver’s car”—raw, responsive, and utterly engaging. Every man should experience what makes this M3 so special.

6. Ferrari F40

The Ferrari F40 is the last car personally approved by Enzo Ferrari. Built to celebrate the company’s 40th anniversary, the F40 is a stripped-down, uncompromising, and brutally fast vehicle. Twin turbos, a lightweight body, and no electronic aids make driving the F40 an intense experience. It’s a true supercar icon, and driving one is a bucket-list moment for any car enthusiast.

7. Land Rover Defender (Classic)

Not all legendary cars are about speed. The classic Land Rover Defender is a symbol of rugged durability and go-anywhere attitude. Whether you’re tackling mountain trails or cruising country roads, the Defender proves that adventure is about capability, not just horsepower. Its utilitarian charm and off-road prowess have made it a favorite for explorers worldwide.

8. Mazda MX-5 Miata (NA)

Lightweight, nimble, and endlessly fun, the original Miata (NA) proves that driving joy doesn’t require big power. Its simple design, manual gearbox, and perfectly balanced chassis make every corner a delight. The Miata’s reputation for reliability and affordability means more people can experience what makes it one of the legendary cars every man should drive once.

9. Mercedes-Benz 300SL Gullwing

With its iconic gullwing doors and advanced engineering, the Mercedes-Benz 300SL set new standards in the 1950s. It was the fastest production car of its time and remains a symbol of luxury and innovation. Driving a 300SL is like piloting a piece of art—the attention to detail and performance are unmatched. It’s a rare treat that stays with you long after the drive ends.

10. Toyota Supra (A80)

The fourth-generation Toyota Supra is a legend in both the tuner world and pop culture. Its turbocharged inline-six engine, sleek styling, and immense tuning potential have made it a modern classic. The Supra is proof that Japanese cars can stand toe-to-toe with the best from Europe and America. It’s a must-drive for anyone who loves speed and customization.

11. Shelby Cobra 427

Brutal, beautiful, and barely tamed, the Shelby Cobra 427 is the stuff of legends. Carroll Shelby’s masterpiece combined American muscle with lightweight British engineering, resulting in a car that’s as fast as it is ferocious. The Cobra’s thunderous V8 and raw driving experience make it one of the most unforgettable, legendary cars every man should drive at least once.

Make the Most of the Drive

Driving legendary cars isn’t just about checking boxes—it’s about understanding what makes each one special. These vehicles offer more than speed or style; they connect you to history, innovation, and the thrill of the open road. Whether you experience them at a club event, a rental, or a car museum, each drive is a story you’ll tell for years.

Which legendary cars every man should drive once are on your list? Share your thoughts in the comments below!