I actually owned a 1994 Roadmaster wagon, which honestly doesn't help my case because I’m not nearly as cool as I aspire to be. However, these cars represent the end of big body-on-frame estates in the U.S., and with a Corvette-derived LT1 V8 hiding under the hood, they went out with a bang in true sleeper-performance style.

Combined with a bulbous shape that’s grown on people through the years, the big ol’ Roadmaster has a cult following that grows larger every day. Even the classic gurus over at Hagerty say now is the time to buy one, because it won’t be long before cars like these are bringing more than $5,000.

The real reason I know these are cool, however, is that a coworker once asked to borrow my Roady to take her teenage daughter and bazillion friends out for her birthday party. Turns out the impressionable youth saw the wagon parked in the lot at work and thought it was way cooler than mom’s SUV. Take that, Lamborghini.

— Chris Smith