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.