Everyone witnessed the trainwreck that was Trinidad James freestyling on Tim Westwood’s show last week. A usually explosive Westwood fell silent, Trinidad James went looking amongst the wall of records to salvage any respectable bars that he could find, and the rest of the hip-hop world wondered if Def Jam was sinking millions into the right investment.
But James isn’t alone. Rappers have bombed freestyle sessions and battles since the art started out in the park—even the best of them. Here, we look back at some of the most tragic freestyles ever recorded to let James know that he’s not alone.