Selected by: Gilles, Mays, van Hooydonk
Original MSRP: $3,215 (1956 356A Speedster model)
Average current value: $183,015 (1956 356A Speedster model)
Porsche Spyder 550
Original MSRP: N/A
Average current value: $3,685,000 (1955 model sold at Gooding & Co. 2012 auction)
Introduced in 1948, the 356 was actually Porsche's first production car and was available in coupe, cabriolet (aka convertible) and highly collectible "Speedster" versions. Mays and Gilles use words and phrases like "stunning,""purity in design" and "simplicity" to describe it. Inspired by the 356, the 550 (pictured here) was a pure racing machine. Van Hooydonk is a 550 fan, noting it's a "true rebel: always open to the elements …" And "rebel" is an appropriate word because the Porsche 550 is the car that "Rebel Without a Cause" star James Dean tragically crashed and died in in 1955.
Selected by: Gilles, Welburn
Original MSRP: $3,465 (1957 model)
Average current value: $61,492 (1957 model with 270 hp engine)
It's probably no surprise that the name "Corvette" appears on our list of best convertible designs of all-time. The real debate could be over which Corvette model years possess the best design elements. Both Gilles and GM's Welburn picked 1950s era 'Vettes. Gilles likes the 1955 for its "unforgettable sculpture and great balance of muscular beauty." These are pretty rare, too: Only 700 were made. Welburn checks the Corvette box with the 1957 (pictured here). He notes that it "was a very pure design statement for the brand." Also of note, 1957 was the first year that fuel injection was an option.
Selected by: de Silva, Gilles
Original MSRP: $7,495 (1965 model)
Average current value: $1,401,450 (1965 427 Competition model)
When you think "Shelby," the first word that likely comes to mind is "speed." Legendary American race car driver Carroll Shelby teamed up with Britain's AC Cars in 1962 to create Cobra. And did they ever go, go, go. After a few years with a smaller engine, Shelby dropped in a Ford 427 rated at well over 400 horsepower, solidifying the brute power of these mighty machines. Gilles points to the "roadster shape [that] has changed lives and hearts forever. It has remained a benchmark in performance and beauty for nearly five decades." De Silva adds: "the American sports car by excellence—a spider that is all muscles!" NBC "Tonight Show" host (and noted car collector) Jay Leno owns a Cobra 427 replica. Shelby died in 2012, but his company Caroll Shelby International (CSBI) lives on.
Selected by: Mays, van Hooydonk
Original MSRP: $6,897 (1968 280SL model)
Average current value: $54,452 (1970 280SL model)
Officially, this roadster is known as the Mercedes-Benz W113. And there were three models: the 230SL (1963-1967), the 250SL (1966-1968) and the 280SL (1967-1971—pictured here). So with all of these letters and numbers, how did this Benz (affectionately) come to be known as the Pagoda? Check out the shape of its (optional) concave roof, which reminded people of curved Far East temples. Van Hooydonk calls the car "beautifully balanced and detailed." Ford's Mays singles out the 1966 250SL as his favorite of the three models.