1986-1995 Suzuki Samurai
Credit: Sermac.gr / Wikipedia

Sure, it's small. Yes, it's prone to dangerous rollovers. And obviously, it makes you look like you're Ken on your way to Barbie's Dream Ski Chalet. But there is something irresistibly go-fuck-yourself about driving a wee cute-ute with a mountain-mounting, low range-equipped four-wheel-drive system. If this were a summer list, we'd recommend you buy one with the plastic convertible top, and we'd suggest that you peel it off and leave it off for good. Instead, you'll want the stylish hardtop. And with $15,000 or less, you can probably buy the best one extant on Earth.