1959 Mercedes-Benz 190SL Roadster
To most people, the 190SL looks almost identical to the 300SLs, which typically go for five or six times what this one's going for. It's got a smaller motor (that whole 190 vs. 300 thing), and it's not as rare (hence the price), which actually makes it one of the better values out there for a classic Mercedes sports car. [More pics...]
Aaron Miller is the Rides editor for Supercompressor. He's a little obsessed, but not in a sitting-outside-the-dealership-at-3a-with-binoculars sort of way. He undergoes track withdrawal symptoms on a regular basis and writes about cars as a salve, and you can follow him on Twitter @aaron_m_miller.