No matter how basic or utilitarian it might be, the Jeep Willys is an icon of cool. Add in some celebrity ownership in the form of actor Steve McQueen, and the value goes through the roof. McQueen is well-known for his love of racing and all things wheeled. From desert motorcycle racing classic sports cars like his Ferrari 275 GTB/4, McQueen owned nearly everything worth driving at one point. While it may not have the flash of its two- or four-wheeled siblings, this 1945 Jeep had a spot in McQueen's collection next to some of the fastest cars of the time. With an expected price of at least $100,000, this is one of the most affordable way to add some of the legendary actor's gravitas to your collection.