The first video I consider to be within the "best of all time" is Get Your Freak On - Missy Elliot. It was directed by Dave Meyers and released in 2001. It is a very surreal performance centred video, with a lot of editing included, including a moment where she spits and the spit flies in slow-motion into a dancer's mouth.
The second video is Rihanna's "Disturbia" from 2008, co-directed by her alongside Anthony Mandler. It was sadistic, dark and edgy compared to usual pop videos at the time, encompassing chains, tarantulas and torture chambers.
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