2001 Mercedes-Benz E55

Fewer than 500 of these naturally aspirated, rear-wheel drive AMGs were shipped to North America during each year of production; the 2001 model is the most rare, with only 366 of them reaching the American market. Perhaps considered a heresy by purists, this particular car has had its original entertainment and navigation system—the COMAND 2.5, which was the most cutting edge tech at the time but now hopelessly outdated—replaced with an extraordinarily powerful stereo system. A large touchscreen Kenwood head unit allows the driver to interface with Google Maps, Spotify, and other apps through Android Auto or Apple Carplay; sound is processed through a Cerwin-Vega EQ; eight JBL woofers and three tweeters powered by 1200 watts of amplification deliver music throughout the interior; 800 watts power a 12-inch Infinity Kappa subwoofer for thick bass alongside a 15-inch Rockville sub, which provides serious low-end punch through a Blaupunkt digital bass processor and 3000 watt amp. The EQ, bass processor, and subwoofer levels are all located within the driver's easy reach beneath the steering wheel for maximum audio control. Though these extensive upgrades may diminish one's appreciation of the upper limits of automobile tech at the turn of the new millennium, they more than compensate by maximizing the modern driving experience to which we've become accustomed.