Elvis Presley and his Pink Cadillac
Elvis Presley owned a lot of Cadillacs, but by most accounts, the pink ones were his favorites. He actually had two pink Caddys. The first was a 1954 that caught on fire in June of 1955. He promptly replaced it with a blue Fleetwood sedan that was even more promptly repainted pink, a special custom shade called "Elvis Rose." (Blue, a perfectly suitable shade for suede shoes, just didn't cut it on the car.) The second pink Cadillac lasted only a couple months -- Elvis' band mate Scotty Moore drove it into a pickup truck that September. It wasn't totaled, though, so Elvis had it repaired and freshly repainted and gave it to his mother. He then bought himself another new Caddy to replace the pink one, even though he also continued to drive the pink one since his mother didn't have a driver's license. He later added a white Cadillac (with a pink roof) to his ever-expanding fleet.
It's a testament to the power of pop music that Elvis Presley and his pink Cadillacs are so intertwined in the public consciousness, even though it seems like he didn't spend all that much time driving them. They were always being repainted, being repaired, or out on loan to a friend or family member. But now the famed pink Caddy rests at Graceland, where it's admired by several hundred thousand guests each year.