3. Jeep Wrangler
Resale value retained after five years: 55.3%
It's loud, it's not terribly reliable, it sucks up gas at a combined 19 miles per gallon and it doesn't store a whole lot unless you get the stretched-out Unlimited version. That said, nothing looks quite like it and nothing's an acceptable off-road substitute at this price. The ground clearance and four-wheel drive come in awfully handy in miserable winter weather, while that removable hardtop makes it a sweet open-air ride in the summer. Car buyers don't pick up a used version of the Wrangler because they want to truck the kids around or make grocery runs. They buy it because they want a "Jeep," and all the frivolities that go along with it.