Clint Eastwood – GMC Typhoon, $29.5K

With a legendary career and an estimated net worth of almost $375 million, this Man with No Name legend earned his top spot starring in the Dirty Harry films and directing the hit Western Unforgiven. Clint Eastwood’s reputed war film Letters from Iwo Jima would even land the icon an Academy Award nomination.

The 90-year-old bonafide Hollywood star is no less of a car enthusiast. Even with the splendid Ford Roadster and Ferrari 275 GTB reigning his garage, Eastwood finds his dream ride in the two-decades-old GMC Typhoon. The Typhoon is a high-performance SUV with a 4.3L V6 engine and is just the kind of speed beast Eastwood likes.