27: 1957 Fiat 500 – $20,100
Minimalist in design like the BMW 300 Isetta, the original Fiat 500 was a compact joy to drive. Seinfeld enjoys the finer things in life and covets a simple car design, hence the Fiat 500. Notable aspects of the car are its compact dimensions and peppy engine. Not missed by most is the fact that the Fiat 500 is increasingly easy to work on, which lends a hand to many not-so-technologically-inclined drivers.

Nevertheless, the Fiat 500 is a suitable addition to a car collection that ranges from the oldest Porsches to the newest exotics. The 1957 Fiat 500 might not look like much, but the car has come a long way in terms of design. Fiat did the right thing when the company introduced this minuscule commuter car.