After watching the music video for Roses by Outkast several more times I found several pictures that are able to tell the story without the entire narrative of the video.
(This screen capture shows that Caroline is in charge of the school)
(Benjamin starts the song by praising Caroline)
(But then the song turns into being about how she needs the best of the best)
(He also emphasizes that she is a "witch" for how she treats everyone)
(The video is rather unclear as to whether Benjamin like her or not because although he makes fun of her, he still fights with Big Boi Freddy Floater for her.)
(The yearbook pictures of Benjamin and Freddy are important to the story because it shows that two popular guys with a lot going for them both like Caroline but she is too blind to see that and she is only looking for what she perceives to be the best.)
(Even while the song is making fun of how vain and selfish Caroline is, she pretends to check herself out)
(Freddy is trying to win Caroline over and is even willing to fight for her but she is still incredibly uninterested in him.)
(Caroline perceives this stranger to be the best of the best and is wooed by what he has to offer)
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