4. Jeff Ross Lays To Waste Flavor Flav And His Vikings Hat

Roast: The Comedy Central Roast of Flavor Flav (2007)
Complex says: In the middle of his set, Jeff Ross asked a important question: “How do you embarrass a crackhead in a Viking helmet?” Well after looking at Flav’s clueless, smiley expression, throughout this epic ribbing, we come to the realization that you can’t.