OVO stands for Octobers Very Own, Drake’s crew. They added the “XO” once Drake linked up with The Weeknd. They made some music together, although now it’s back to being OVO again after they separated somewhat acrimoniously (Drake disses him on 5AM in Toronto (French Version)).
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He feels like she can’t be impressed by the things he does, he is nervous that she has seen all this before, from other guys she might have cared more about. This is the theme of the whole song.
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It’s not a metaphor to going underground. As you can see in the next line, he answers his own question saying they may have found a body. This implies that “Why a nigger go south” is a rhetorical question stating why black people have to run away. It is because they are being falsely accused of crimes.
