They may be big shots in the music industry now, but everyone has to start somewhere — why not the Grammys? Some first-time attendees get lucky and win their first Grammy at their inaugural awards show. Billie Eilish won her first five trophies at the 2020 ceremony when she was just 18 years old, breaking several records. “That s*** was f***ing crazy,” Eilish told Vogue days after winning her Grammys. “If anything, it’s an exciting thing for the kids who make music in their bedroom.