1999 MTV Video Music Awards – Lil’ Kim Face Transformation

Although Lil' Kim is rocking bright purple hair in this photo, it is one of the photos that introduced us to how she looked at the beginning of her career.

With a hit debut and being one of the world's leading female rappers at that moment, the then 25-year-old Kim looked fresh-faced and as natural as one can get with a wig on. Obviously, her outfit that night made more headlines than how many of her wrinkles were starting to show.