Cadillac Eldorado Biarritz [1959]
Credit: Getty Images

Number made: 99 (est.)
What one will cost you: $60,000-$100,000
Horsepower: 345
Engine size: 6.4 liter, overhead-valve V-8
Top speed: n/a
0-60 mph: 10.3 seconds

History: After '59, Cadillac tail fin height ebbed, and with it went the buckets of chrome. The Cadillacs of the sixties grew more staid and introverted, which shouldn't have been allowed to happen.

Design: In the fifties optimism was measured in tail fins. And in no car were the tail fins taller, sharper, or more hopelessly optimistic than in the 1959 Cadillacs. The Biarritz was chosen for this list because it was arguably the most outlandishly chromed and pointy creation to issue from American styling studios in the entire decade. The Eldo channeled the mentality of excess that would lead not only to tail fins tall enough to provide shelter for elves, but a car-naming strategy that needed both the Spanish and French languages to get its point across. Yes, this was the most luxurious, over-the-top machine of the jet age, and its swagger was the source of its sexiness.