By Jamil Weeks

Every generation, hip hop fans are catered to an epic contest of wits amongst rap’s heavyweights placing bids for their claim to the throne. In the 80’s, we had the Bridge Wars. The 90’s gave birth to coastal wars that spiraled into dangerous terrains. Millennials got to experience Jay-Z and Nas during the 2000s “Star Wars”. Just last year, two of rap’s current biggest stars, Drake and Kendrick Lamar, engaged in a colossal assault on each other’s character. The all-out dogfight has become the biggest rap battle ever witnessed. As Kendrick is enjoying the spoils of his triumph with his victory lap of a nationwide and international tour, rappers from everywhere are issuing challenges and calling out names hoping to duplicate Kendrick’s results. Nas has found himself in the crosshairs of multiple rappers. Beef was cooked into the Clipse rollout. Nicki Minaj is stirring the pot with everyone on social media. Joey BadA$$ took on an entire coast! Things are only heating up for the summer. While none of these potential squabbles have succeeded in capturing my interest, they did jog memories of rap battles I always wanted to see but never materialized. These possible skirmishes could have altered the trajectory of many careers. The speculation makes for an intriguing discussion on feasible outcomes.

Big Daddy Kane vs. Rakim

The battle between Jay-Z and Nas was a spectacle to behold in real time. A contest between two superstars highlighting a clash in styles. Versatile artistry from one of rap’s biggest stars versus lyrical complexity from one of rap’s greatest poets. Their dueling musical approaches draws parallels to a pair of 1980s GOATs. Big Daddy Kane and Rakim are the 80s equivalent to Jay and Nas respectively. Kane was a champion of clever punchlines and double entendres making his music more accessible to a broader audience. Rakim’s conversational delivery and Five Percenter spirituality elevated lyricism and songwriting in rap to new heights. With competing forms of artistic expression, naturally came the comparisons as the two were pitted against each other in fiery debates amongst fans. The bickering amongst fan bases must have put the battery in each artist’s backs. We came close to a Kane and Rakim battle actually happening. Tensions heightened as their rivalry became increasingly more heated. Rakim recorded a record, the unreleased “Break the Wrath in Half”, dissing Kane by name. Kane planned to respond with a record of his own. Before matters got too out of hand, a mutual acquaintance, Ant Live (Eric B’s brother), arranged for the two to have a conversation. The two legends ironed out their differences and battle plans were scrapped. While Kane and Rakim avoided a confrontation, the arguments continue today over who people think would have won this battle for the ages.

The Weeks Prediction

If the two battled live in front of a crowd, the edge leans towards Kane. Kane was a dynamic performer who could not only rap but was also talented as a dancer. His charisma and humorous wit might have been enough to win over the crowd in comparison to Rakim’s more subdued performance style. However, I could imagine Rakim coming up with a sinister clap back capable of piercing through Kane’s soul. The Jay and Nas battle is proof to never underestimate the writer’s pen.

2Pac vs. Ice Cube

West Coast icons, 2Pac and Ice Cube, share many similarities. Both rappers turned actors dominated rap in the 90s. Each rapper started their careers in a group before embarking on their solo journeys. Their music blended hardcore street and introspective socially conscious messaging. Both are responsible for releasing arguably the greatest and most disrespectful diss records ever recorded. With both being West Coast deity, comparisons between them organically sprouted. Although Pac and Cube were once cool with each other, competition breeds envy. Pac became one of the biggest stars in music once he joined Death Row. As both vigorously represented the West Coast, friction formed between them. Pac felt Cube was riding his wave taking on the East Coast on behalf of the West. Pac stated in an interview that Cube was never as aggressive in standing up for the West until he saw what Pac was doing. Pac believed Cube throwing up the W’s was a gimmick to sell records. Rumors circulated that Pac was ready to give Cube that Biggie treatment. A potential matchup between these two would have been an epic showdown. Unfortunately, Pac was murdered before the battle fully came into fruition.

The Weeks Prediction

Cube was no stranger in engaging in verbal combat with former friends or allies. He dissed his former group, NWA, and clashed with Cypress Hill. Cube even dissed his own cousin, Kam. However, this was post-prison Pac. Pac emerged from incarceration in war mode, mashing on anyone over perceived disrespect. With his passionate delivery and venomous fury, that might have proven to be too much for an Ice Cube who was no longer in his prime. If I were a betting man, my money would be placed on Pac for the win.

Nas vs. The Notorious B.I.G.

Before the infamous battle with Jay-Z, Nas almost publicly traded insults with another Brooklyn emcee. The Notorious B.I.G., alongside Nas, was an instrumental leader for 90s East Coast rap. Biggie introduced the East to a formula showing them how to balance the artistic scales between hardcore and radio-friendly. Both alumni of the class of 1994, Biggie and Nas individually dropped back to back classics out the gate. While they were cordial as artists, they both also had their eyes set on the crown. Similarities in the album covers for their debuts led to a weird energy between them. Biggie found himself on the receiving end of a scathing Ghostface rant off an Only Built 4 Cuban Linx album skit. Ghost accused Biggie of biting the Illmatic album cover. With Biggie stealing the spotlight from Nas with a more commercial sound, Nas was forced to evolve for the sake of his career. Enter Escobar season, where friendly competition escalated to growing animosity. Warning subliminal shots aimed at each other were surfacing. By the time the two had their last encounter in Los Angeles, both camps walked past each other without speaking. At the same time, Nas peaced it up with Pac as Big aligned himself with Jay with plans on forming a super group, The Commission. Lines were being drawn in the sand. The competitive nature of hip hop would have certainly led to one of the most ferocious displays of lyrical dexterity. With Big’s tragic passing, not only were we deprived of a generational talent but also of what could have turned out to be an all-time slugfest.

The Weeks Prediction

A battle between these emcees in their prime would have been riveting. Nas is someone you do not want to back down in a corner. However, listening to “Kick in the Door” and “Long Kiss Goodnight” is a reminder how hard it is to fathom any emcee getting the best of a Biggie unloading a clip from his lyrical repertoire. The charm and humor combined with THE illest flow gives Big a strategic advantage to snatch victory from Nas.

Dip Set vs. G-Unit

With the turn of the century, 2000s hip hop was dubbed as “The Mixtape Era”. The budding mixtape scene was dominated by two crews out of New York. The Harlem-based Diplomats, a.k.a. Dip Set, and the Queens collective, G-Unit. These two factions flooded the streets with classic mixtapes that rivaled a lot of rappers’ studio albums. G-Unit was the biggest entity between the two. Backed by the Interscope/Aftermath/Shady conglomerate, G-Unit’s reach was longer than their more regional Dip Set counterparts. The Dips made up for it by catering to the sensibilities of rap fans below the Mason-Dixon Line, amassing sizeable southern support. Bumping heads between the crews was inevitable. Both group leaders, 50 Cent and Cam’ron, were very outspoken and crew members were highly protective of their brands. When 50 referred to Koch Records as an artist graveyard, Cam took exception given his business ties to the label. A spat between the two took place live on the radio when Cam called to voice his displeasure with the G-Unit general. Soon after, the two traded barbs with each other on official diss records. Fans eagerly anticipated mixtape wars between the crews, wondering when each team’s members would join in on the fun. 50 managed to throw a monkey wrench in those plans. In a shocking move, Dip Set’s capo, Jim Jones, made an appearance with 50 on Rap City at the height of the beef. Jimmy previously was a Dip Set enforcer who inherited Cam’s beefs with rival rappers, such as Mase and Nas. Dip Set was never the same after that Rap City episode aired. Rap fans were left out in the cold, leaving them to ponder who would have prevailed in this hip hop battle royale.

The Weeks Prediction

The matchup between both teams was pretty even. In addition to Cam versus 50, imagine Juelz versus Banks. Imagine the trash talk between Jimmy and Yayo. The difference is resources. With Dip Set going a more independent route, it is hard to believe they could have withstood the Iovine/Dre/Eminem machine as they were seen as the industry’s biggest bodyguards. In the end, G-Unit’s popularity would have been enough for them to advance past the Diplomats.

Black Thought vs. Nas

Two of rap’s premier wordsmiths found themselves on opposite sides around the time of the Jay and Nas beef. In an attempt to sabotage the release of the Nas comeback album, Stillmatic, Jay decide to release an MTV Unplugged version of The Blueprint on the same day. The band performing acoustic versions of Blueprint songs was none other than The Roots. As Jay and The Roots performed “The Takeover”, where the Roots played an interpolation of the Nas classic “NY State of Mind”, it was seen as them publicly siding with Jay in the battle. Feeling slighted, Nas publicly criticized The Roots referring to them as hypocrites. Nas had also previously been critical of The Roots appearing in black face in the Spike Lee film, Bamboozled. In an interview on Hot 97, Nas labeled the Philly group as “porch monkeys”. Black Thought responded to Nas questioning the validity of the conscious subject matter in his music versus who he is in real life. After calling Nas a fake Muslim, the two rappers found themselves under the same roof at a Talib Kweli show. As Thought recounted, he was prepared for anything that evening, including potential violence. However, both emcees had a conversation and were able to come to a mutual understanding. Otherwise, the feud would have certainly risen to a war of words on wax. If that had happened, rap fans would have enjoyed the most lyrically proficient rap battle from two masters in their craft.

The Weeks Prediction

With both artists recognized as virtuoso talents due to their skill sets, this matchup is tough to gauge. Nas is extremely battle tested. Thought’s vigorous style of rhyming and technical versatility in rhyming might have been the difference in victory or defeat. Thought most likely escapes with a win by the thinnest of margins.

***** Honorable Mentions *****

1) 2Pac vs. DMX
2) Boogie Down Productions vs. The Entire Juice Crew
3) Eminem vs. Any Top 10 Caliber Emcee
4) Jadakiss vs. Jay-Z
5) KRS-One vs. LL Cool J

As long as hip hop exists, so will the competitive spirit that pushes its participants to be the best versions of themselves. The drive to be the best leads to artists not seeing eye to eye. Sometimes these situations get resolved before becoming a main event prize fight. Sometimes fate works against these battles transpiring. The artists mentioned have all made substantial contributions to the genre. Makes you wonder how a victory here or a defeat there would have affected the musical direction of the genre. These artists lay it all on the line with these rap battles. Risking damage to their careers and reputations with every misunderstanding with a rival, these battles do have lasting effects in some cases. Ja Rule and Drake are prime examples of how taking a loss can affect an artist’s stature and bottom line. As a fan of hip hop since the 80s, it is fun to reminisce of old quarrels that have taken place in rap over the years and make logical predictions on who would emerge from the ashes as the victor. As much as I wanted to see these battles, I am equally satisfied in watching some of these artists patch things up and work together. Kane and Rakim have become friends. Cam and 50 have become supporters of each other’s business ventures. Nas and The Roots have performed together on multiple occasions. Always great to see growth and maturity in rap artists that oftentimes is overlooked in favor of peddling negativity amongst the artists. What are your thoughts on my predictions? What rap battles did you want to see since you discovered rap? Drop your comments down below!