Kelley Blue Book Value: $8,691
Engine: 3.2-liter V6
Some might be surprised that you can get a Caddy for less than $9,000, but the CTS is a great first ride, if you're looking for a little more spacious four-door. The CTS was the beginning of a cool new wave for Cadillac that left the "old people cars" notion out back with the scrap metal. Plus, with a more sophisticated sporty look, you might catch the eye of that fine ass sociology teacher from third period.