Macy Gray Awards

2000
Brit Awards for Best International Newcomer and Best International Female

MTV Video Music Award for Best New Artist ("I Try") and for Best Cinematography ("I Try")

VH1/Vogue Fashion Award for Most Fashionable Artist - Female.

Billboard Music Video Award for Best Pop New Artist Clip of the Year ("Why Didn't You Call Me").

2001
Grammy Award for Best Female Pop Vocal Performance ("I Try")