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.

Knockout Punch: “Run in ya house, cover ya mouth with masking tape/ let my chick strap on a dick, ya ass get raped”- Cassidy

Murda Mook vs. Jae Millz

Millz was seeing a little bit of fame after his Making The Band appearance, so it makes sense that folks would be coming after him. This would become the prototypical Smack DVD type battle that would flood the net for a couple years. Each MC brought a slew of punchlines that we could probably find on some freestyle buried on a mixtape. Mook, though spits like the hungry MC and actually has some bars especially prepared for Millz.

Knockout Punch: “You the hottest out? Please J/ You lost to a nigga that walked to Brooklyn for cheesecake”- Murda Mook

Remy Martin vs. Lady Luck Part 1 Part 2

Remember when Remy used to be known as a rapper? In case you forgot, here’s the proof. The first battle was a draw as these two ladies gnarled and spit at each other. The beauty of this battle is that it took off once each contestant decided to toss out the writtens and go off the top. The second time around, Remy showed why people were calling her a great female MC at one point.

Knockout Punch: “I can tell you been drinkin 40s/ look like you pushin 40/ got like 4 kids then tryin to be somebody shorty? Stop it”

Serius Jones vs. Jin

See rule #2. Jin was definitely at a disadvantage due to the fact that Jones had a lot of fodder as a result of Jin’s failed rap career. I mean, dude already had an album out and was competing for 10 G’s? Things got ugly quickly as Jones used the race card to cut the hell out of the deck. Jin declared that this was unfair, but the fact is Jones ate dude up without the racial jokes. This battle put the final nail in Jin’s coffin and launched Jones’ career.

Knockout Punch: “You been wack ya whole career/ Ain’t there like 2 Billion people in China? You can’t go platinum over there”- Jones

And since I know someone is gonna get ignant and put it in the comments:

Eli Porter vs. Envy

Knockout Punch: “You already in the Gay parade!!!!”

Share any more famous battles and link em up!

Previously Posted — D-Block Vs. Rocafella | TSS Presents 15 Minutes With EnJ

Stray Shots

Hollyweerd – Edible Phat: The Mixtalbum

Trackstar The DJ – Still Dreamin 3

Chill Rob G – The Power 12″

Flying Lotus – Shhh! (2008)

Flying Lotus – Los Angeles (2008)

King Syze – The Labor Union (2008)

Lords Of The Underground – Here Comes The Lords

Ol Dirty Bastard – The Dirty Story : The Best Of Ol Dirty Bastard

Okayplayer – True Notes Volume 1

Busta Rhymes – I’ve Already Outshined Your Favorite Rapper Mixtape

Scarface-Last_Of_A_Dying_Breed

Big_Mike-Still_Serious

Stray Shots