Dennis Rodman – Age 59
You would never have guessed that Dennis Rodman grew up as a shy kid. However, after being picked in the NBA draft of 1986, he made his way up as a professional basketball player. Through the years, Rodman’s appearances drastically changed as he became comfortable with large facial piercings and tattoos.
During his career, the 59-year-old has won five NBA Championships before retiring in 2006. Rodman has also had involvements in the wrestling industry and film, where he starred in Double Team and Simon Sez. In 2020, he launched his very own clothing line named Rewear.