Jay Leno – 1955 Mercedes 300SL Gullwing Coupe – $1.8 Million

Jay Leno’s cherry-red 1955 Mercedes-Benz “300SL” Gullwing Coupe is still one of the most coveted automobiles in the world, with an estimated value of $1.8 million in 2023. This iconic car is known for its sleek design, innovative engineering, and impressive performance. It was developed initially as a racing car, and it won numerous races in the 1950s.

He regularly drives it and shows it off in his popular YouTube series, “Jay Leno’s Garage.” While maintenance costs for a classic car like this can be high, Jay says it’s a small price to pay for the joy of owning one of the most iconic cars ever made.