Top Ten Rap Battles in History


To the casual observer battle rap might seem like an anachronism, until you realize that it’s bigger than ever. Leagues like URL and King of the Dot have produced some of the most talked about events in hip-hop — with the controversies to boot. (And the parodies.)

Battling has gone from a niche interest to an important part of hip-hop culture. For those new to the scene, however, here’s some historical perspective: the 10 greatest rap battles in history.

10) Illmaculate vs. Swann 2004 The early 2000s battle scene’s greatest prize was the coveted Scribble Jam trophy. The annual Columbus, Ohio battle saw the best freestyle battlers in the country square off in a one night tournament. The first round of 2004’s event saw the previous year’s finalist Swann upset by Illmaculate, making his debut, who went on to take the event’s top honor.

9) Eyedea vs. P.E.A.C.E. 1999 The battle that certified Scribble Jam’s prestige was the 1999 incarnation, between L.A.’s Freestyle Fellowship luminary P.E.A.C.E. and upstart Minneapolis wunderkind Eyedea. It was one of those cross-generational torch-passing moments, and helped make Scribble Jam a showcase of freestyle greats for most of the coming decade.

8) The Saurus & Illmaculate vs. Quest McCody and Marv Won (Battle 2) 2007 UK-based JumpOff.TV hosted scored battle leagues, and took it international with two World Rap Championship tournaments. The most anticipated showdown occurred in the semi-finals as the previous year’s winners Illmaculate and The Saurus faced Detroit’s Quest McCody and Marv Won. The second meeting between the two teams is regarded as JumpOff’s finest hour.

7) Iron Solomon vs. Math Hoffa 2007 Among the most disputed and influential battles ever was Smack’s match-up of Iron Solomon and Math Hoffa. Solomon had defeated Jin the previous summer, and Math had punched out another rapper mid-battle, so anticipation was high. While Solomon was arguably at his peak here, Math’s approach — playing to the camera — changed the way battles are performed and presented.

6) Loaded Lux vs Calicoe 2012 Last summer saw the return of veteran battler Loaded Lux, as he took on respected URL wordsmith Calicoe. Part of Summer Madness 2, arguably battling’s biggest event yet, Lux’s entertaining theatrics did little to unnerve Calicoe, who even endured Lux’s jaw-dropping one-of-a-kind progressive final round.

5) Dizaster vs. DNA 2011 For nearly five years, Canada’s King of the Dot league has produced some of battling’s most exciting match-ups. Perhaps its finest hour (as host Organik and special guest Drake witnessed) was the 2011 battle between Dizaster and DNA. With approaches in each round as diverse as their styles, these two put on an absolute clinic that was hailed a classic.

4) Juice vs Supernatural 1999 Throughout the ’90s, depending where you were, the word “freestyle” called to mind either Supernatural or Juice. Finally, at the Wake Up Show’s Ninth Anniversary party, the ultimate dream match took place. In front of one of the most hyped crowds to ever witness a battle, the back-and-forth became regarded as the definitive rap battle for years to come.

3) Kool Moe Dee vs. Busy Bee 1982 This was not only the most influential rap battle of all time, but one of the most important moments in hip-hop history. It took place at Harlem World in 1982 when Treacherous 3 member Kool Moe Dee decided to combat chief party-rocker Busy Bee’s crowd pleasing call-and-response rhymes with his own brand of super-personal, complicated rhyme schemes. The battle became one of the most circulated live bootlegs ever recorded and was the first step rap took towards advancing the art form of lyricism.

2) Murda Mook vs. Serious Jones 2006

While the 2003 battle between Murda Mook and Jae Millz was the first widely circulated must-see street battle of this era, Mook’s later match-up with Serious Jones cemented the format as one to be taken seriously. Exemplifying the charisma that draws battle fans in and delivering with two flawless performances, it’s one of street battling’s first masterpieces.

1) Dumbfoundead vs. Tantrum 2008

This was the show-stealing match at Grind Time West’s inaugural Battle of the Bay event. There’s a reason Dumbfoundead vs. Tantrum has become known as the go-to battle to convert new viewers into battle fans. Wildly hilarious, incredibly innovative and capturing the fun vibe that keeps people coming to battle events, it put Grind Time on the map and signaled a change in the way the world viewed rap battles. Almost five years later, the event still holds up as a perfect storm of sharp lyrics and unforgettable performances.

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