James Lipton
Perhaps one of the most surprising facts on our list, we have James Lipton, who, in the 1950s, actually worked as a pimp. Yes, you read that correctly. The host of Inside the Astors Studio admitted that while he was a resident in Paris in the 1950s, this was his occupation for some time.
James even explained that after World War I, things were different and that pimps in France more closely resembled their employers than their exploiters. Even though it appears times were much different, the fact that he was a literal pimp still blows our minds to this day.