9. Model Thirty

Year: 1912
Complex Says: Every winter, you should think of the Model Thirty and be thankful that you're not standing outside in the snow cranking your engine to life. The Model Thirty ushered in the era of the electric starter and "[opened] up the driving experience to women." This may sound horribly sexist today. But if you think about the culture in 1912, no lady would be caught dead cranking a motor. This was the second Caddy to win the Dewar Trophy for technological contributions to motoring.