BING CROSBY — CADILLAC 1947, EST. $3,195
If you grew up in the 1940s and 1950s, you would probably recognize Bing Crosby as the singer of White Christmas and as someone who co-acted in a number of movies with Bob Hope. However, many film buffs of today don’t know that Cosby was an avid golfer and a gearhead, too.
Crosby, who left for his heavenly abode in 1977, amassed a lot of wealth in his bank account and snapped up a Cadillac 1947 at one point, which was one of the hottest automobiles in the 1940s and 1950s. He had to shell out approximately $3,195 for the car, and if you think that’s a pretty small amount, consider the fact that one dollar in 1947 is equivalent to twelve dollars today.