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#11 Soulja Boy "Crank That" -- Best Rap Song (2008)

The "Best Rap Song category" is the one cat where overall musicianship and the production of a track is weighted just as much the rest of the song’s appeal. So it makes sense why in 2008 songs like “Big Things Poppin’” by T.I., “Ayo Technology” by 50 Cent and Justin Timberlake, “Can’t Tell Me Nothin’” by Kanye West, and the category’s winner “Good Life” also by Kanye West, were featured. But Soulja Boy and musicianship go together like, well, like hip-hop and the Grammys. See what we did there?