Lilly Singh — Late Night Host at 30

Lilly Singh tops $16.5 million in annual earnings. Starting as YouTube's "Superwoman" with 14.7 million subscribers, she became the first openly bisexual woman of color to host a major U.S. network late-night show, NBC's A Little Late with Lilly Singh, earning the $16.5 million Forbes reported in 2017. Her New York Times bestseller, UNICEF partnership, and multi-network production deals have sustained her income since the show ended. Unlike many influencers who rely solely on brand deals, Singh's ability to pivot between platforms—from YouTube to late-night TV to producing—has built a more resilient career. While Khaby Lame's silent videos earn $16 million annually, Singh's diverse portfolio proves that longevity in entertainment depends on crossing into Hollywood, not just dominating one platform.