Trinidad James "Pound Cake Freestyle"
Date: October 2
This is what the fifteenth minute of fame sounds like. In a terrible display of freestyle rhyming, Trinidad James tried to rhyme over "Pound Cake" while on Tim Westwood's show and it can best be described as a trainwreck. So bad that it's hard to watch (sadly, more people probably watched this than all of the rest of these freestyles combined). Trinidad had nothing to rap about and could barely string two bars together. The thing about freestyles is, you have to actually come off the dome—if you don't, no one will really care. So we really have no idea why Trinidad thought he had to keep it 100. Maybe if he had written some rhymes, he wouldn't have embarrassed himself. — Insanul Ahmed