Bruce/Caitlyn Jenner – Age 72

While Bruce Jenner should have been primarily famous as an Olympic gold-winning decathlete for the US, he became an even bigger name internationally when he and his family were featured in the long-running reality show, Keeping Up With the Kardashians.

After divorcing matriarch Kris Jenner, Bruce came out as transgender and underwent gender re-assignment surgery. She changed her name to Caitlyn, and finally felt comfortable in her skin. Bruce was a fan of Botox back in the day, and so is Caitlyn, now!