Words By David D.

I stumbled upon the “Stylin’ On You” video the other day on Youtube and was reminded how much I used to love watching freestyle battles before that classic moment in goon history essentially ruined it for me. But for a time, I was on YouTube non-stop checking for these battles as they are good showcases in punchline rap. Although in order to fully enjoy these contests you gotta understand a few points:
1) These cats aren’t freestyling. These are mostly old, rehearsed bars with the opponent’s name inserted whenever the rapper has a little extra space. And if the battle’s been scheduled for a long time, chances are that the opponent-specific bars were rehearsed and planned days in advance as well.
2) The more famous rapper is at the disadvantage. If I battled Lil’ Wayne, I’d have tons of funny things to say cuz I know so much about his life. Wayne doesn’t know anything about me and has substantially less material to go on.
3) Ignore the crowd reactions. I don’t know how these signed guys have such a large posse, but they do- and each posse member has to show up for the battle. You can tell by watching because they’re the guys screaming at the top of their lungs as if “you’re ugly” is the hottest punchline ever.
Now that you know the rules, enjoy some memorable face-to-face battles.
Cassidy vs. Freeway Part 1 Part 2
This one wasn’t fair from the start. Freeway isn’t a battle rapper and rarely has any punchlines- plus his strength is dependent upon his ability to ride a beat. So an acapella battle with Cassidy resulted in one of the most one-sided ass whoopin’s in Hip-Hop history. This video launched Cassidy’s legend and was the precursor to a lot of the Smack DVD battles that would flood barbershops across the hood. Read the rest of this entry »