Battle rap has a history filled with classic moments made by pioneers of the sport, so its hard for someone new to come along and cement their spot as a legend.  From 2008 on, a lot of newcomer top-level talent had wowed the fans with spectacular performances, but Hollow Da Don always seemed to stand out with his unique style.  Every top level emcee has a  “God Moment” that has them shining like Zeus sitting atop Mt. Olympus - this was Hollow’s.  He could do no wrong; this is the battle that had people questioning whether or not Hollow Da Don is the best battle rapper of all time.

Side Note: The more you watch this, the more you realize that Big T had some dope bars, but Hollow’s performance was just too much.

Memorable Moment: “Nigga that’s the Don’s shit!”

 

Way before Arsonal battled Conceited, this was the original longest battle in history.  I used to hate this video because these two LITERALLY battled from high noon til night time and I have selective A.D.D (lol.)  Also, I could never tell who was winning.  Mook got away with saying he won some of these long battles because he always seemed to take the later rounds due to his incredible stamina.  R.I.P Party Arty aka P80 who showed up and did WORK on SMACK DVD after a clutch undefeated streak in Fight Klub.

Memorable Moment: “When I was in Rikers, you was in diapers” - we may also have to give Arty credit for being one of the first emcees to spit the “jew(el)s/holocaust” line.

Usually, battles on tv suck - they make our culture look stupid, have dumb rules and feature people that are not considered top level emcees by battle fans.  Diddy was cosigning Jae Millz heavy at the time and really wanted to get the Harlem street legend some major exposure.  There was a few episodes of the original season of MTV’s Making The Band that featured all of the emcees having to battle to earn their spot in the group.  Babs beat Mina and Mysterious convincingly, which caused Diddy to make her battles Ness for 3 rounds - the footage was never released and a winner was not declared.   Choppa and Fred battled for 41 minutes in a match that ultimately ended up a draw.  In a main event of sorts (that occurred on a separate day), Puff brought in Jae Millz to battle E. Ness - a battle which he judged personally.  The rounds went as followed: 1 - Millz,  2 - Ness, 3 - Draw, 4 - Diddy stopped the round and called the whole battle a draw, hoping both emcees would blow up off of the footage.  Lil Wayne ended up signing Jae Millz to Young Money years later after he remembered seeing this battle on MTV.

Memorable Moment: Millz’s 4th round (“fuck!”) ... one of the best verses in battle history - you can read more in depth about it here

1997 Scribble Jam is one of the most celebrated and well known battle events of all time for two reasons: Juice’s dominance & Eminem’s main-stage battle debut.  Any time a battle that was meant to be two rounds ends up being a 6 round tie breaker, chances are it's a classic.  Juice went on to win the whole event.

Memorable Moment - This one is a tough call, but I may have to say the 5th round.  Eminem debuts his famous “you wouldn’t sell two copies if you pressed a double album” line, while Juice kills it with the “Rap wackness/Robin Harris” bar.
 

Dizaster and Okwerdz were probably the most hated battle emcees in New York for at least two years because of the “coast banging” and constant shots they threw at rappers from the mecca.  When Poison Pen announced that Dizaster would be traveling to NY to battle Swave Sevah, it easily became one of the most anticipated battles in NY history.  Nobody in that crowd wanted to see Diz win - not only was he battling one of the most respected emcees in New York, he had also been physically threatened constantly throughout the night.  At the height of the battle, Dizaster managed to diss a heckler in the crowd with a freestyle, then refocus his energy on Swave - a performance for the ages.  To further add to this classic moment, Swave managed to spit two great verses and bring the battle down to the wire.

Memorable Moment - Dizaster DESTROYING the heckler in the crowd
 

The highest viewed battle in King of the Dot history - a match that made Drake skip out on Future’s video shoot to be front and center.  People love to argue about the winner - Dizaster had one of the best verses in history with his first round, but DNA seemed to match his intensity and was able to steal the crowd, even after Diz’s Prince of Persia rebuttal in the second, so its a close call.  Only thing I would change about this battle is the time limits; they seemed to run out of steam and resort to freestyling the third, which took away from the first two classic rounds.

Memorable Moment -

“I do this for my fans, you mutherfuckers ain’t shit to me/

Are you kidding me? Im fuckin’ bum rushing a enemy//

These knuckles will leave you buckling instantly/

Y’all fuckin’ get timid, i'll start punching you viciously//

Uppercuts will leave your stomach in misery like muscular dystrophy/

Just for thinking you can come online publically dissin’ me//

You can pop your fist im still crushing you physically/

This shit is child’s play - you’ll get ate (eight) sideways like the number infinity//

You need artist development before you come on a blog and then mention me/

I'll stomp you out and make you a part of this history//

*Points at the time clock* Don’t show me that cause this is about to be the bodybag of the century/

*Hold on, hold on* You muthafuckers ain’t shit to me, they say karma’s a bitch, for you its probably dentistry//

Case the part of your mouth that’s missing is only a reflection of what’s scaring you mentally/

So, the gap in between your teeth exists merely as an object of imagery to distract you from the real gap between us and that’s BARS AND DELIVERY!//”

Those 14 bars prove why Dizaster is one of the freestyle and written battle king’s.  DNA surviving that onslaught is a testament to his skill level and composure.
 

This may be the most quoted battle in history.  Everything about this battle is classic: from the bars and crowd reactions to the back and forth arguing between Mook and Serius.  This was the Fight Klub king against the king of street battling - I don’t know if the fans even saw this one coming.  The biggest argument about this battle has always been the crowd and whether or not they were unfairly over-hyping Mooks lines because he had all his people in the building.  Jones claimed that he was only there with three of his people, while Mook claims Jones was lying, as he had people in the room, but they were not making noise.  Who knows?

Side Note: Peep a young Mickey Factz in the crowd with the glasses & first ever white cell phone headphones LOL

Some Thoughts: A lot of people wanted to see Mook loose - he turned into public enemy number one.  Jones brought real talk, bars, jokes and freestyles in an attempt to downplay Mooks character.  A lot of fan’s sided with Jones, but Mook had some of the craziest bars we had heard to that date (ie “Bet your own shadow will want to walk across the street from you.”)  I’ve been starting to wonder if the crowd ended up hurting Jones or Mook more in the long-run.  The “circle/square,” “two L’s like Cool J,” and “now back to regularly scheduled programming” lines were all invented in this battle and were reused many times throughout history.  I wonder how the crowd would have reacted to Mook’s “Saigon did the P’s - I’m about to do the F’s” portion if Serius had not interrupted Mook for going over three minutes.  Guess we’ll never know - great battle.

Memorable Moment - SMACK getting a close up of that nigga’s tight ass jeans (were they even tight?)

Serius Jones’ defining moment.  Jin was the champ - he was beating everyone with freestyles and premeditated rhymes and had won over 50K doing so, until he met up with Jones in the finals of a four man tournament that saw himself, Too Much (UK Champ that slapped Saint on Jumpoff), Streetz The Block (106 Champion), and Serius Jones facing off.  In the first round, Jin won a highly debatable battle with Streetz saying “RZA heard him rhyme and walked away,” while Jones easily outclassed Too Much with rhymes like, “For the bread i’ll pop the toaster and burn this lil English muffin.”  In the final round of the tourney, Serius caught what might have been the worst and most significant body in history, as it was featured on outlets like BET and MTV and played a role in Jones’ signing with Ludacris’ imprint, Disturbing Tha Peace, which was immensely popular at the time.

Memorable Moment - “You ain’t no Ruff Ryder - you be on the back of the bike huggin’ on like one of them broads” - *dead*
 

This is the best battle in Scribble Jam history.  You have an unknown kid from Australia win a prelim battle and all of a sudden be face-to-face with the favorite to win in a classic semi-finals match.  This may actually be the best PURE FREESTYLE battle of all time, as the rebuttals and on-the-spot observations were crazy.  Justice won after a few extra rounds, but fans argue that The Saurus may have won in regulation time.

Memorable Moment - “Australian? A less distinguished version of an English person” may be one of the top 10 punchlines ever, but this back and forth is what made the battle classic:

The Saurus: “Good day mate, you need to vacate / cause based on your time zone you’re a day late”

Justice: “Yea I’m a day late and thats the reason for your fuckin’ mothers period”

CRAZY

If this list didn’t count historical value and just focused on BARS, this may probably be the best battle of all time.  During a period where battle rap is oversaturated, its not often that one video comes out that everyone labels a MUST SEE and has fellow battle rappers raving over its replay value.  This is some of the best wordplay and schemes hip hop has probably ever seen in general.  The impact JC and Chilla had on up-and-coming emcees and the battle game in general is mind boggling, that’s why the match almost no one saw coming is currently sitting at over 650,000 views.

Memorable Moment - JC’s second round flip on Chilla’s style:

“He wifed a bitch on facebook and I bet you goin’ regret it too/
Cause she just tryna get poked, so she’ll (social) network til we all get f’n blew (blue)/”

That shit was nutty!