I always tell people that Fresco is one of the best battle rappers of all time, but due to his High School Musical-esque appearance and bass-lacking voice, some may take him as a joke.  On paper, the man has some of the most intricate, funny, and hard hitting material that I have ever heard.  Soul Khan is an emcee that puts his heart and soul (no pun intended) into his music, but has seemed to create an alternate persona/style perfect for battle rap.  The man demolishes his opponents and has won over every single battle rap crowd and demographic.  This battle is a classic match thrown together by Poison Pen for New York’s “7/30” event.

Memorable Moment: Soul Khan singing

Kap Kallous pushed for a lot of battles to happen for GT’s Grizzlemania 2 event.  He claimed this one would steal the show - as always, Kap was dead on.  Swave’s slow, articulate, and calculated flow seemed to be just as effective as Syd’s aggressive, joke-heavy style.  Haymakers, hilarious moments and arguably the best scheme in battle history make this match one of the top 30 all time.

Memorable Moment: “I’m just comparing his bars to mine”
 

Any time two close friends or family members battle, it always makes for a great show.  The world was shocked when Pat and Hollohan agreed to battle each other, but it quickly became (arguably) the most anticipated match in canadian history.  If you don’t think Pat is one of the top 20 battle rappers all time, you need to watch this immediately.  

Memorable Moment: “Beats the shit outta me”

This is THE rap battle.  Any hip hop historian or person that calls themself an “emcee” should not be allowed to rap if they don’t know about Juice vs Supernat.  These are two of the best freestylers of all time - this battle didn’t raise the bar; it WAS the bar.  Most sources only seem to have one round of the battle, but if you look hard you can find all three.

Memorable Moment: Juice’s tetris line, “You couldn’t reach the top on a bad game of tetris.”  A lot of people seem to be captivated by Supernat’s stage presence and performance back then, but if you listen really closely, you will realize that Juice was performing on a level that people may not have been able to fully appreciate or understand until recent years.
 

Fresh off of Arsonal’s Fight Klub win over Hollow Da Don, Lush One wanted to reach out and get Ars his debut Grind Time match.  I can remember being on the phone with Lush for hours discussing who the best opponents could be, when he mentioned the name “Okwerdz.”  I thought it was a strange match, but Lush continued to say that Okwerdz really wanted a chance to prove himself against such an opponent and put the whole Fresh Coast on his back.  I guess Lush decided to make it happen.  This battle re-sparked the competitive East/West hip hop feud that had interested audiences worldwide in years prior.  So many classic lines in this battle - not only was it Okwerdz’ defining moment; it was when battle rap became interesting again.

Memorable Moment: “What a buncha divas!”
 

Unbeknownst to most, Dizaster and Nocan had battled twice before this, so this meeting was the final chapter.  This performance is the reason why Dizaster’s name is at the top of the battle ladder - he went to a level that most are incapable of.  Nocando, known by many as the best freestyler in the world, somehow was able to creatively match Dizaster intensity with fierce freestyle.  This is the BEST BATTLE I HAVE EVER SEEN LIVE.  Mixing written with freestyle and having under a week to prepare isn’t for the faint-hearted - this is how you live up to your name and far exceed expectations.

Memorable Moment: The whole battle; shit was amazing.

After two or three weeks on 106th and Park, the world did not think that Jin could be beat.  His fifth week in, Jin would face his toughest opponent of all - Skyzoo.  This battle really showed how amazing and on point Jin’s freestyle ability was at the time - the performance was unbelievable.  I can recall my friends and I downloading this battle and memorizing all of the words, just like any popular song from the radio or tv.  Skyzoo’s (now) status in hip hop as a premiere lyricist, mixed with Jin’s international celebrity solidify this as a classic match - it shows how hungry emcees can progress beyond battle rap.

Memorable Moment: “You rap like AJ dress dog ... terrible”

When Big T and Surf couldn’t go down on the stage at URL’s “Motor City Mayhem” event, they decided to take the battle back to glory days of SMACK and hold it in the “Burn Rubber” clothing store.  This battle was perfect: the crowd wasn’t too big, the BARS were crazy and the match is highly debatable.  This is one of the top 10 battles in SMACK/URL history.

Memorable Moment: Big T’s Keenan Ivory Wayans line - a perfect mix of creativity and crazy wordplay
 

Ever since Math battled Dose and opened with, “I was supposed to battle T-Rex but he was scared,” the stage was set for one of the most hyped battles of all time.  To further add the the mayhem, the battle was supposed to be held on Grind Time, but after things didn’t pan out, it ended up being SMACK’s entry back into the battle world with the Ultimate Rap League.  This battle always causes an argument - did Rex win the first two rounds or was Math’s third one of the best rounds in history?  

Memorable Moment: Math’s 3rd round

Murda Mook was as big as SMACK DVD itself at the time and became an underground celebrity by battling top names around New York City, some people even thought that he couldn’t be beat.  Loaded Lux seemed to come out of nowhere and just completely take Mook’s thunder with a very charismatic performance.  Mook claims that SMACK DVD didn’t originally show the whole battle, which made it seem like Lux won.  URL re-uploaded all 8 rounds of the battle in 2010 and still has fans arguing over who won.  The match transcended battle rap and solidified its spot as one of the most memorable videos in hip hop history.  

Memorable Moment: Lux’s first round “Goddamn it, this niggas parents smacked some shit up on his face!”