Tiffany — 47, Boutique Owner & Singer

Tiffany Darwish, known by the mononym Tiffany, became famous for her 1987 cover of I Think We’re Alone Now. It became a teen anthem and she gained huge fame as a singer and songwriter. She’s had her ups and downs since then, including a legal battle between her manager and her mother and father over the control of her earnings and her career. Tiffany also appeared in her fair share of movies and TV shows such as That ’80s Show. She owns a clothing boutique as well but hasn’t given up on making music. Her studio album Pieces of Me was released in 2018.