Winner: Soul Khan
Year: 2010

There's a lot to see in this 15 minute battle between Grind Time emcees Soul Khan and Madness. Yes, Madness perfectly reenacts Soul Khan's "Holdonholdonholdonholdonholdonholdon." And yes, Khan perfectly slices and dices Madness' rotund belly with lines like, "You got the abs of Schwatzenegger when he was pregnant in Junior." Khan lunges after Madness when he says, "See Grind Time owes you nothing, up in all of your vids/So get the fuck over yourself, Tony, the rest of us already did."

It's fascinating to see Madness flame out in the second round. And yes, it's laugh-out-loud funny when Soul Khan spits, "It's like your dinner is played by Nicholas Cage: it's gone in 60 seconds." But the best reason to watch this video is for Poison Pen's (He's in the Grind Time shirt) reactions to punchlines.