The 10 most epic URL battles of the Smack/YouTube era

by Keane Eacobellis

There was once a time when the modern world of battle rap was a secret culture known only to its enthusiasts. Of course, the art of battle rap itself has been well-known for over three decades, but battle rap culture is something else entirely.

Now considered a sport, battle rap has grown into a big business where top rappers are seen as prized fighters in their profession, drawing thousands of people to watch two lyrical behemoths attempt to verbally destroy one another on stage. Complete with analysts, media personalities, and running narratives, battle rap has turned into a dramatically intense event that has created its own niche in entertainment.

The popularity of the sport has gotten so huge that even the OVO boss himself, Drake, has partnered with the URL to reach a wider audience by streaming their events for free through the Caffeine app.

You may remember the early days when BET’s 106 and Park had aspiring rappers battle each other on Freestyle Fridays for the chance to be recognized by the world. If you’ve seen Eminem’s 8 Mile, then you know something about how the battle rap scene used to be. You’ve also more than likely seen the celebrities duke it out with each other on James Corden’s short-lived Drop the Mic series with Method Man and Hailey Baldwin (now Bieber).

But despite what you’ve seen, that is still not quite the battle rap culture that stands today. Before we look at the current state of things, let’s first take a look at how battle rap began.

The origin of battle rap

It first started in the midst of the ’80s east coast hip hop scene, when MCs like Kool Moe Dee and Busy Bee Starski faced off to throw their best material at each other while the crowd determined who was the better rapper. Starski’s gibberish and comedic performance style was soundly defeated by the more complex raps of Dee and changed the standard of what it took to be an MC.

Before their legendary battle, the prestigious title of MC was usually given to the crowd-pleasing comedian who was able to perform well on the beat. Thanks to Dee, the title of MC was transferred to the performer who was able to be both commentator and storyteller. For Dee, it was simply a point to make. Little did he know that he and Bee’s battle would end up birthing an entire world in hip hop that’s still thriving decades later.

Full of braggadocio and laced with quirky personal attacks, the art of battle rap soon became extremely popular as part of hip hop’s underground scene. Somewhere along the way, it became an unspoken rule that to be a commercial rapper, an artist needed to come prepared to battle another rapper at any given moment. 

It even set a standard as to how good you really were with the art of hip hop. Being able to rap well both on records and in person against other emcees usually illustrated that you were a well-rounded artist. It got to the point that aspiring emcees even walked around with a few battle-formatted bars in their notebooks just in case they needed to display their proficiency with the art, like samurais concealing specially-made swords until the moment called for them.

Battle rap & the industry 

What many people may not realize is that battle rapping also inadvertently helped to change the way future generations of artists approached the art of rap itself. What started out as friendly party-themed songs performed by local street-savvy slick-talkers-turned-stars was soon transformed into gritty tales filled with aggression, verbal acuity, and versatile deliveries aimed to assert one’s dominance as an artist.

Even today⏤though it’s nowhere near the same level⏤trap music still thrives off the braggadocio, dominant demeanor, and aggression that goes all the way back to the battle between Kool Moe and Busy Bee ages ago. The mood in rap changed, and battle rap is one of the biggest reasons for that.

The beginning of battle rap culture

Later on, in the mid-to-late ’90s, Troy “Smack” Mitchell from Queens, New York introduced the Smack DVDs⏤compilations that featured music from upcoming artists and rap battles from underground rappers well known in the streets⏤to various parts of the United States.

In the beginning, battlers like Murda Mook and Serius Jones simply met up at barbershops or street corners to film a battle, with only 50 or so people in attendance as bystanders. Over time, the popularity of the Smack DVDs eventually helped Mitchell build the Ultimate Rap League, a battle rap organization that pays aspiring battlers to perform in front of packed crowds at official venues. Mitchell first introduced his Ultimate Rap League on the Smack DVDs, but after YouTube began to gain popularity, he switched over to streaming on the platform. 

Now, almost two decades later, The Ultimate Rap League, or URL, has introduced some of the most entertaining and exciting battle rappers to ever grace the stage. With so many battle rappers in the profession, the URL has become something of its own universe⏤similar to the WWE⏤and with that universe comes its own etiquette, slang, and characterizations. Thanks to the sport’s aggressively competitive nature, these battlers are constantly butting heads, which, luckily for us, has provided some of the greatest matchups in battle rap history. 

Before we get into this, there’s a few things you need to know. First, these battles can be derogatory in nature, so if you have delicate ears, this may not be your cup of tea. Second, there are so many stars who have battled in the URL that it can be difficult to keep up with everyone. Instead, we’re going to take a trip through the URL’s YouTube era, covering some of the sport’s biggest stars who helped build the URL platform to what it is today. And third, just like any other sport, battle rap has its own brackets and player stats that are governed by a system of categories based on certain factors. 

Let’s do a loose rundown of how the battle rap system works.

Battle rap styles and ranking

In the world of battle rap, battlers fall under several categories, including anglers, schemers, punchers, lyrical linguists, and gun bar kings. Outside of that, you have battle rappers who are well-rounded enough to meet the criteria from multiple categories, making them dangerous and difficult opponents to defeat.

Then you have the top-tier, mid-tier and low-tier battlers. The top-tier category consists of rappers who have consistently performed at a high rate and have shown to be in high demand. They’re the ones you see consistently getting booked on the bigger events (or “cards,” as they’re called in battle rap). Mid-tier battlers are usually the ones on the rise and have strong enough content to keep up with top-tier battlers, but not quite enough to defeat them⏤that is, unless it’s an upset and a top-tier battler was having an off day (which happens). They have a reasonable demand but have not yet drawn enough of a following to headline an event. The lower-tier battlers are mainly the ones that have either lagged behind in standing or have what is considered to be “weaker content” compared to a mid-tier battle rapper.

Warning! The following footage contains strong language, mature themes, and violent content. Viewer discretion is advised.

Tay Roc vs. Hollow Da Don, Summer Madness 6

One of the most anticipated battles of URL’S YouTube era, Tay Roc vs. Hollow Da Don, was a clash of styles. Known as the Gun Bar King, Tay Roc’s style of rapid punches, metaphors, double entendres, and extremely aggressive delivery was put to the test against Hollow Da Don’s style combination of creative punches and witty comedic angles.

During this timeframe, Hollow Da Don was already considered a seasoned top-tier vet from the earlier days of the URL’s YouTube era. After taking some time off, Hollow returned to the URL to test his skills against the Smack’s next rising star, Tay Roc.

At this point, Tay Roc had already solidified himself as a top-tier battler, and when you become a top-tier battler, part of having that position means you have to face the legends. Back then, depending on the outcome, Roc was either going to get demoted or retain his spot amongst the top-tier rankings. Spoiler alert: he’s now considered one of the greatest of all time in battle rap history.

Charlie Clips vs. T-Rex

At URL’s Fourth Summer Madness, Smack decided to pit Harlem rappers Charlie Clips and T-Rex against each other for a friendly yet exciting exchange. This is also one of the few times where Charlie Clips had a near-flawless victory for all three rounds against a battler considered to be a lower tier than him. In battle rap, it’s usually not entertaining to watch a one-sided battle, but this one was so funny that even T-Rex was enjoying himself.

Well-known for his four-bar buildups and freestyle ability, Charlie Clips is a battler who uses witty wordplay, humor, a calm demeanor, and strong punchlines called haymakers to thoroughly break down his opponents. His career on the URL has been quite impressive and his ability to improv a rebuttal is so legendary that it eventually landed him a spot on Nick Cannon’s Wild ‘N Out. Thanks to that, he’s one of the most recognizable battle rappers in popular culture.

DNA vs. Ill Will

At URL’s Nome 4 event, rising star Michigan battle rapper Ill Will faced off against the young legend DNA from Brooklyn. Considered one of DNA’s finest moments in battle rap, the battle between the two was a heavy exchange of schemes and punches that seemed to rock the entire building.

Ill Will’s charisma and gritty street bars kept him in the fight, but it became a completely different story once DNA began to get fired up. Well-known for his ability to freestyle and rebuttal his opponent’s content at any given moment, DNA turned the tide with the crowd with an explosive display of lyricism and creativity that was just too well-executed to deny.

K Shine vs. Calicoe

A battle between regions for URL street cred, the exchange between Harlem’s K Shine and Detroit’s Calicoe was a test of the delivery as both rappers were renowned for their swift flow approach, gritty punchlines, and street talk. Both battlers were well-rounded with angles and punchlines aimed to break down each other’s stage personas and their regional acquaintances. 

During this time, both battlers were rising stars thanks to their equal levels of aggressive and witty wordplay. This is also the time that the Midwest Movement (St. Louis and Detroit) were on a tear to prove that New York was not the only area that bred top-tier battle rap talent. One of the most entertaining battles at the peak of the URL’s YouTube era, K Shine vs. Calicoe is one of the greatest milestones in URL history.

Arsonal vs. Hitman Holla 

One of the first Smack battles to be featured on YouTube, the clash between New Jersey’s Arsonal and St. Louis’s Hitman Holla is still credited as being the first to draw YouTube audiences to the URL. Already an established heavyweight battler from his time in explosive runs at The Lion’s Den and Fight Klub, Arsonal was heavily favored to have a clear win against Hitman Holla, who was then an underdog debuting for the first time on the URL stage. 

However, the St. Louis battler proved the critics and fans wrong when he not only showed his ability to control the crowd, but proved that he could keep up with Arsonal for every round with his gritty street punchlines and commandeering delivery. That’s tough to do against Arsonal’s metaphorical, alliterative, and often disrespectful rhymes. Honestly, just hearing Arsonal crush someone else’s soul is enough to make you want to curl up and die.

Conceited vs. Tsu Surf

This battle of the double entendres changed the course of battle rap. In terms of delivery, it popularized the use of double entendres and set the precedent for how it was delivered. Brooklyn’s Conceited was notable for his constant barrage of humor, similes, analogies, metaphors, double entendres, and triple entendres, making him one of the most dangerous opponents when it came to punchlines. On the other side, New Jersey’s Tsu Surf was also noteworthy for his analogies and double entendres but was considered the underdog due to his level of punching power. A grudge match to determine the true master of flipping double entendres, the battle between Conceited and Tsu Surf is one of the more epic battles in terms of content. 

Double Impact: The Emergence of 2v2 Battles

As the URL became more popular, battle rap squads composed of multiple battlers also began to emerge in the profession. After a while, the groups became so dominant that the URL began hosting 2 on 2 battle events to allow the teams to compete for bragging rights, which he called Double Impact. At the time, Team Homi was the largest and most dominant battle rap crew in the culture, but that all started to change when DNA and K-Shine decided to form NWX. 

Similar to the WWE wrestling ensemble, NWO, the duo of DNA and K-Shine, was a radical addition to the URL that many would say revolutionized 2v2 battles. Both were amazing battle rappers who were already difficult to defeat separately, but as a unit their synergy made them even more of a threat lyrically. Their creative, well-choreographed performances were consistently an experience worth seeing and their level of content seemed to reach new heights every time they faced a new set of opponents. As far as records, they were pretty much unbeatable in any 2v2 setting, making them the most dominant force in battle rap for a long time.

As their popularity grew, more battlers joined NWX and soon the duo turned into an even bigger battle rap ensemble than Team Homi. Of course, it didn’t take long for other battle rap teams to come out of the woodwork to dethrone NWX, spawning even more groups hoping to dominate the URL. Squads like Writer’s Block, EFB, Team Homi, and The Goonies all began throwing shots at each other, but only one squad had what it took to truly give NWX a run for their money: the duo of Tay Roc and Tsu Surf as GunTitles. 

Tay Roc & Tsu Surf vs. K-Shine & DNA

A clash of titans for the ages, NWX vs. Guntitles was a heated and highly-anticipated grudge match, as both teams were evenly matched in punchlines, levels of content, and performance. Out of the two groups, NWX were the more polished veterans after already having been on a tear for over a year, whereas Guntitles was relatively birthed for Tay Roc & Tsu Surf just so they could have their first official 2v2 battle with NWX.

Guntitles’ drive to face NWX came partially from mounting tensions between K-Shine and Tay Roc that originated from a dispute over their mutual past with another battle rap group, Dot Mob (which is a story for another time). With both battlers known to be aggressively high-strung and ready to snap at a moment’s notice, the air between Guntitles and NWX was almost on fire.

The battle was so heated between the two sides that a fight broke out and the event was cut short due to emotional difficulties. However, the two squads faced off again at a later date to close the chapter on the rivalry they started in a battle that fans still perceive as one of the best 2v2 battles to this day.

Chess & Steams vs. Quest McCody & Marv Won

As the URL’s 2v2 battles grew in popularity, other battlers moving up in the ranks used the 2v2 events to show off their skills and rep their respective groups. In this battle, the team of CakeLyfe⏤composed of battle rap star Chess and his partner Steams⏤faced off against Quest Mcody and Marv Won.

Seen as one of the best battles on the Double Impact Card, Chess & Steams’ mixture of aggressive wordplay and unorthodox performances made them one of the best 2v2 teams on the bracket, while Marv Won and Quest Mcody were battle rap vets whose lyrical wordplay and witty approaches could shake a room when the group was at their best.

Both teams were evenly matched in terms of punchlines, but Chess & Steams were already the heavy favorites given Chess’ status as a rising star in the future of battle rap. Luckily for the crowd, the battle was not as one-sided as many expected and the culture was treated to one hell of a classic.

T Top & Brizz Rawsteen vs. Chilla Jones & B Magic

The trend of rookies vs. vets continued with this battle between Chilla Jones & B Magic of Writer’s Block vs T Top and Brizz Rawsteen of DarkLyfe. For Writer’s Block, Chilla Jones’ slow-angled approach and complex schemed punchlines were seen as a possible threat, while B Magic’s creative punch heavy flow was considered a dangerous compliment to his partner’s more complex style. 

However, both battlers were seen as low-to-mid tier in the URL and had seemingly been shelved on the roster for years, making them the underdogs against the rising stardom of Darklyfe. In Darklyfe’s case, T Top’s witty performance, gritty street content, and smooth punchlines made him a top competitor in the URL, while his partner Brizz Rawsteen was also on his own rise to fame with his disrespectful in-your-face approach and violent punchlines. Both battlers were on a tear in the singles division and, at the peaks of their respective careers, were seen as heavily favored to win their bout as a duo against Writer’s Block. 

An exciting matchup of new school vs. old school, the battle between Writer’s Block and Darklyfe was another clash of the “ages” that provided some of the best 2v2 moments from T Top & Brizz

Ill Will & Rum Nitty vs. Math Hoffa & Cortez

Another clash of rookies vs. vets, this battle pitted Troy Mitchell’s early Smack Era of pioneers against his new URL Era phase of stars as OG spitters Math Hoffa and Cortez (formerly NYB) against Team Homi’s top gunners Ill Will and Rum Nitty. For both Math Hoffa and Cortez, it had been a while since their momentum during the Smack Era, yet fans still highly anticipated their return to the big stage.

Back during his heyday, Math Hoffa was a well-known legend for his intimidating stage presence, edgy street content, and hard-hitting punches in the ring figuratively and literally. The man has actually punched people in the face during battles. His partner, Cortez was also a reputable battler known primarily for his slick talk, angles, and street relatable punchlines.

Across from them stood Team Homi’s most recognizable members, Ill Will and Rum Nitty. At the time, Ill Will had shown impressive skill in previous battles as a singles competitor using his humor, aggressive street presence, and witty punchlines to take the crowd away from his opponents. His Team Homi comrade Rum Nitty had risen quickly to fame for his aggressive performance, witty street schemes, and unique delivery of punches. 

Though this battle was anticipated to be a good matchup, no one was prepared for the many great moments it produced. In the end, it turned out to be one of the more entertaining 2v2 battles during the early days of the URL’s 2v2 events.

There are so many facets of the battle rap culture to be explored: the fashion, slang, etiquette, the beefs, and of course, the battlers themselves. Then there’s the history: the Smack DVD era, URL/YouTube era, and the New era. And let’s not forget the latest news on the drama that unfolds in and outside of battle rap. Battlers tend to make references to those types of things, so you’ll want to stay tuned in if you want to understand what’s going on when they do.

If you’d like to read more about all things battle rap, be sure to let us know in a comment below!