Madonna and Debi Mazar
In the 80s, Mazar and Madonna found themselves in a nightclub in New York City. Mazar was trying to make it as an actor, doing makeup work to pay the bills, and Madonna was trying to make it as a singer. They kept in touch, and Mazar ended up doing makeup for Madonna in several music videos, as well as performing in said music videos!

This picture was taken at Don’t Bungle the Jungle in 1989, a concert to raise money and awareness about saving the various rainforests of South America. Madonna performed for the benefit concert, and Debi Mazar was along for a big greeting at the end. The two still remain friends, and I can only imagine all the crazy stories they can tell together.