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Originally posted by IVY
Because MTV is an ass and they've always ignored her videos for some reason.
Heart breaker was released in 1999
It definitely deserved to be nominated instead of beautiful stranger, have you seen that video? 
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According to Wiki the video premiered around mid-August 1999, which means it would've been eligible for the 2000 VMAs, not the 1999 ones--which helps explain in part why it was snubbed, since it was fairly old by the time of the 2000 awards. Still, I don't know if it would've made it against this competition:
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Best Female Video (2000)
Aaliyah — "Try Again" *WINNER*
Christina Aguilera — "What a Girl Wants"
Toni Braxton — "He Wasn't Man Enough"
Macy Gray — "I Try"
Britney Spears — "Oops!...I Did It Again"
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Not including other female videos that also received nominations in the year 2000 like Lauryn Hill's "Everything Is Everything," P!nk's "There You Go," "J.Lo's "Waiting for Tonight," etc.