31. Madonna and Dennis Rodman

We are not sure if we could ever forget about these two getting together. Madonna and Dennis Rodman will forever be one of the most controversial couples of all time, credits to both of their fame and success in each of their fields.It all started in 1994, when Rodman was one of the brightest stars when it comes to the sports of basketball. Madonna was already the queen of pop, and so she has decided to have her crush invited over to her mansion. Rodman received the invitation and as he got there, dozens of people were waiting in the lawn, the garden, and the backyard with cameras and setting up for a photo shoot.

The diva came out and they had an instant public display of affection even before they were able to speak to one another. All of the pictures were kept by Madonna. They dated for two months. Rodman recently revealed that Madonna was willing to pay him $20 million to have his child.