49. TLC "Unpretty" (1999) 

Director: Paul Hunter
Album: FanMail

This video for this No. 1 hit cost $1.6 million to produce for a reason. It's an amalgamation of everything that TLC stood for in their biggest decade. The clip weaves multiple narratives involving women with self-esteem issues, and shows how they overcome them. Chilli's boyfriend wants her to get breast implants, Left Eye's crime-ridden neighborhood has her down on her luck, and T-Boz is bullied because of her race—but they all persevere. And with such a massive budget, the triumph of each woman looks beautiful, too.  -Ernest Baker