Justin Timberlake, by far. His sole memorable video was Cry Me a River, which was only so because of the blatant Britney lookalike. Mind you, he didn't deserve VotY that year either and he ended up going home with that too
Timberlake by far. How he got it before Kanye (even though it was only a year) is unbelievable.
I think in terms of cultural relevance (at their peak) it's Britney>Kanye>Beyonce>>>>Timberlake. Nsync's videos are more iconic than his solo ones and everyone knows it
These are the titans of pop stardom. All of them deserved their award. I mean come on, videos like Toxic, Single Ladies, Power, and Cry Me A River
with that pseudo-Brit, oooooh
: iconic.
