Bill Cosby | BMW 2002 TII | $84,000

American stand-up comedian Bill Cosby held a very active career that spanned over six decades. His beginnings were as a stand-up comedian in San Francisco during the 1960s and worked his way up to having his own sitcom, The Bill Cosby Show. His own TV program was the launching pad of several celebrities who also made it big later on. Cosby, however, was not all about comedy. He also took a serious view of education and finished his doctoral degree from the University of Massachusetts Amherst.

Now of advanced age, Cosby appears to be behaving like a doting grandfather and telling stories. One of those stories he would tell was experiencing discrimination by being given a red Cadillac Convertible by a boss. He asked for another car and got a Ferrari. Now, Cosby can afford any type of car, including one of the more expensive ones, such as the vintage BMW 2002 TII.