SARAH MCLACHLAN
From her lack of number-one singles to her creation of Lilith Fair, the female-only music tour, acoustic singer-songwriter Sarah McLachlan has always remained outside of the realm of the traditional music industry. Thankfully, she always received the support she desired. “My label gave me complete freedom,” McLachlan told Lenny Magazine. “[They] didn’t tell me what to wear, or how to cut my hair, or ‘Can you open up those top two buttons on your shirt, please?’”

These days, McLachlan continues to thumb her nose at what people expect of pop stars by frequently posting selfies without makeup on. It’s clear to see why: McLachlan has aged flawlessly!