16. Billie Eilish – $25 Million, Ocean Eyes
Billie Eilish revolutionized pop music by refusing to conform to traditional industry standards. The Los Angeles native was just 14 when Ocean Eyes went viral on SoundCloud in 2016, launching an unprecedented career trajectory. By 18, she’d swept the 2020 Grammys, winning all four major categories—a feat only achieved by one other artist before her. Her whisper-soft vocals and dark aesthetic created a completely new template for pop stardom.
Now 23, Eilish has become an advocate for body positivity and mental health awareness, frequently discussing her struggles with depression and body dysmorphia. Her signature oversized clothing style was initially adopted to avoid being sexualized, though she’s since explained it also reflected her comfort levels. When she shares makeup-free selfies, her striking green-blue eyes and natural freckles become focal points. She’s spoken about having Tourette syndrome and how accepting her differences has helped her embrace her authentic appearance. Her pale complexion and unique features need minimal enhancement—the heavy eyeliner and neon hair colors she sometimes sports are artistic choices rather than necessities. She represents Gen Z’s rejection of impossible beauty standards, showing millions of young fans that looking “different” can be powerful and beautiful.