The Rap City Freestyle Awards: An Absurdly Detailed Investigation

From Bow Wow perplexing to Cam'ron floating, this is the best and worst of BET's hip-hop time capsule.

There are avenues of hip-hop nostalgia that we as lifelong fans will gladly travel down until the end of time. For those of us who grew up in the age of mid-2000s hip-hop, BET’s Rap City was one of those familiar streets, packed to the brim with history and visual artifacts, that we can now revisit with just a few keystrokes and access to YouTube.

The appeal of Rap City lay in its momentousness as a legendary hip-hop time capsule. Coupled with 106 & Park, it felt like the epicenter of the expanding web of hip-hop, with its alluring guests, unregulated interviews and discussions, and its most master of ceremonies Big Tigger (who hosted from 1998-2005). The show connected the different threads of that web and pulled together something wonderful in the flourishing days of BET as a formidable music network.

Specifically, though, Rap City became legendary because of its “Freestyle Booth” segment, in which the guest artist would step inside the booth and lay a “freestyle,” pre-written or not, over whichever beat was played. In reality, there were more freestyles recorded than we ever aired. Yet, we have watched those made available to us for over a decade without ever thinking to contextualize their time and place in history.

For as magical as they were in the moment, how do we determine the well-aged from the absurd, the silky smooth from the awkward, and the most egregious from the most important? I’ll give you the answer: we come up with awards for all of them.

Welcome to the Rap City Freestyle Awards.

The “Whose Mans Is This?” Award: Bow Wow

Making fun of Bow Wow has become too easy at this point. Almost as easy as, say, Googling "private jet flight picture" to pretend to stunt only to get caught in coach. Yet, despite how things have turned out for Shad Moss, he was quite the rap star in the early to mid-2000s. In fact, his Rap City freestyle is one of the most viewed on YouTube, which is what actually makes it one of the most perplexing.

Clearly borrowing from both the concept and cadence of Notorious B.I.G.’s “Just Playing (Dreams)" while rapping over Chingy’s “Right Thurr” instrumental, Bow Wow’s verse contrasts as much with the present Bow Wow as a Michelangelo painting, except if you were watching the painting melt right in front of you. With lyrics such as, “J-Lo, mmm I don’t know, I don’t wanna go where everybody been,” Bow Wow spends the majority of his verse dogging popular women in entertainment who are, mostly and unsurprisingly, still much more famous than him. What remains even more strange is the said use of Biggie’s concept from Ready To Die’s bonus track. Why didn’t he just rap over the “Just Playing” instrumental? Why does he rip his shirt off at the end like it’s holding him back lyrically? Why is Big Tigger seemingly way too hyped up? These are mysteries that will never be solved.

The Most Awkward Rapper Pairing Award: 50 Cent & WC/Snoop Dogg & Talib Kweli (Tie)

For this award, there were actually two winners. The first, 50 Cent and WC, feels eerily like a WC appearance that 50 Cent was contractually obligated to appear in. Although the East Coast/West Coast feud was in hip-hop's rearview mirror by this point, one can’t help but feel like the contrasting styles of WC’s sporadic and particular flow and 50’s molasses delivery don’t make much sense together, and it doesn’t help that 50 completely mails in his verse.

The second, Snoop Dogg and Talib Kweli, another LA-NY pairing, once again finds the West Coast emcee at the top of his game over an incredibly well-timed “Wanksta” instrumental, while Talib Kweli, the superior emcee, fumbles his cadence all over the place. Although Snoop’s raps often drift dangerously close to a street remix of "The ABCs," Kweli, one of rap’s finest lyricists, grabs the baton from Snoop only to drop it, accidentally drop kick it into the stands, and blind a popcorn vendor.

The Next-Day Shipping/First-Class Mail Award: JAY-Z

Rarely did artists come on Rap City and completely mail it in when it came to the freestyle booth, and rarely would it have been an artist with JAY-Z’s stature. Yet, surprisingly, the freestyle that stands out the worst in terms of effort is Hov’s freestyle over Ludacris’ “Stand Up” instrumental.

Despite ending his verse on a much more positive, original note, it’s hard to look past the fact that Jay raps his entire first verse from “Public Service Announcement” in place of something unheard. It isn’t just the recycled verse, a tactic used several times on Rap City to varying degrees, but the fact that this particular verse from “PSA” sounds so much more rushed and uninteresting when made to fit a different skin. If not for the Big Tigger T-Mobile Sidekick plug at the beginning, this video would stand as Rap City’s most overrated moment.

The Most Distracting Freestyle Award: LL Cool J

In any other scenario, LL Cool J rapping over Eminem’s “The Way I Am” beat, dissing Jamie Foxx with lyrics about being “a pussy, busta ain’t funny as Chris Rock” would sound like pantheon material. Instead, LL, and his biceps, decided to do the freestyle sitting on the booth’s toilet for, you know, symbolism purposes. It’s the type of “doing too much” mentality that has often gotten in the way of LL’s own shine, and a perfect encapsulation of how to self-sabotage your own amazing lyrics by providing cheap gimmicks. I shouldn’t be spending my time trying to figure out if his pants are on instead of listening to his lyrics, but that’s exactly what happens every time.

Side note: Raekwon also pulled this same stunt a year prior, but, somehow, he just made standing on the toilet feel like a natural boss move.

The Most Likely To Make You Punch Your Screen While Watching Award: Fredro Starr and Sticky Fingaz



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You’d be hard-pressed to find to more energetic souls in the hip-hop history books than Onyx’s two most prominent members, Fredo Starr and Sticky Fingaz, whose turn on Rap City was as hyped as the booth may have ever been. It isn’t until Sticky’s mind-melting verse, sprinkled with jabs at everyone from 50 Cent to Ja Rule, that one starts to lose actual, physical control of their bodily functions and starts uncontrollably throwing things around the room by video’s end.

Most Underrated Freestyle Award: Cassidy

This was one of the hardest categories to decide on, with contenders like Boot Camp Clik’s freestyle over 50 Cent’s “In Da Club” beat and Method Man’s freestyle both coming close to winning. Yet, once Cassidy, equipped with Obie Trice’s “The Setup,” began rapping, “I’m in the presidential, gettin Lewinsky baby,” the rest of the competition felt lacking. Cassidy’s lyricism was perpetually masked by his corny hit singles and finite levels of charisma. Yet, when it came to pure lyrics and punchlines, the Rap City booth only amplified a severely overlooked skillset.

Most Overrated Freestyle Award: The Game, Busta Rhymes & Reek Da Villain

There are hundreds, literally hundreds, of freestyles that tried to master Lil Wayne’s “A Milli” instrumental from 2007-2008, and most of them crashed and burned gloriously. One of those unfortunate freestyles came from two of the more interesting rappers of their time, The Game and Busta Rhymes, and what we were given was a half-assed, awkward moment that found the two legends handing most of their time off to Reek Da Villain to shine. To paraphrase what Regina George once said in Mean Girls: Stop trying to make Reek Da Villain happen. It’s not going to happen!

The Lyric That Sounds the Most Like It Was From the 2000s Award: Ludacris

During one of his several appearances, Ludacris once rapped, in regards to a rhyme scheme about holding Big Tigger for ransom, “Bring Free, Sanaa Lathan, and a bottle of gin.” If you showed a hundred kids born after the year 2000 pictures of Free from 106 & Park and Sanaa Lathan, it’s bound to turn out like that scene in Super Size Me where the little kids couldn’t tell the director who was in the picture of Jesus. We are really, really old.

The Best Big Tigger Outfit Award: Twista Freestyle

Big Tigg’s throwback Len Bias Maryland jersey looks so pristine, one almost can’t even pay attention to the fact that Twista’s verse doesn’t even have a beat behind it. Tigger was always known for not only having the flashiest clothing on the show, but he also serves as an artifact of that decade through each and every outdated outfit. Yet, it was the Bias jersey, a simple ode to a fallen prodigy, that actually felt more important than the rapper freestyling in front of him.

Most Consistent Guest Rapper Award: Ludacris

Another close contest, one that saw Cam’ron, Lil Wayne, and Juelz Santana coming dangerously close to taking the belt, but in the end there was only one rapper who never needed home runs every freestyle to prove his worth. Ludacris, appearing four times, three alone and one with his DTP label members, had a style that meshed perfectly with what made the booth freestyles so electric. It was punchline-heavy, well-crafted to fit any instrumental, and evolved even further the minute Luda’s signature cadence and charm arrived on the scene. Even Big Tigger looked like he was having the most fun whenever Luda showed up.

The Worst Freestyle Award: Ying Yang Twins & Lil Flip

There is a world in which the Ying Yang Twins made their hit records, walked away with all of the riches of their wildest imaginations, and never bothered us again. Then, there is the reality we live in, where they, along with Lil Flip, once tried to spit bars over Scarface’s “Guess Who’s Back” instrumental. Spoiler alert: it didn’t go well.

The Best Freestyle Award:  Cam’ron w/Dipset

Nothing, I repeat nothing, has ever been more fun to watch in the history of YouTube videos than watching Cam’ron, in a pink tee and pink bucket hat, count a hilariously large stack of hundred-dollar bills while rapping an immaculate verse over Scarface’s “On My Block” beat. It’s a moment in time so precious, I, for one, would be willing to pay for access to continue viewing it if it ever comes to that.

With lyrics like “You got heart, fight me/I dearly depart wifey” and “With the SK, doggie I’m OK/my AK was my AKA before my ABCs, that had me A-OK,” you actually start to notice yourself floating above the computer chair by the time Cam reaches the pearly gates of freestyle rap. It’s a testament to how effortless he makes something so perfect sound that a viewer like me tends to forget Jim Jones and Juelz Santana are even in this video, despite also having great verses. If there ever comes a time, say, in 50 years, when you need to introduce Cam’ron to a friend, this is the video you turn to.

The Most Important Freestyle Award: Lil Wayne

It’s ironic that the most important Rap City freestyle is neither the best recorded nor one that even contains Big Tigger, as Q-45 had taken over hosting duties by this point. Yet, from the minute that Lil Wayne and Birdman cover the mic in a red bandana, and the minute Wayne begins his verse with, “Live from the 504...," it felt like the world shifted.

Yes, it was a verse that would be released a month or so later on his Da Drought 3 mixtape, but it isn’t the freestyle itself that makes it so important. Instead, what this particular moment in Rap City history represented was the first tremor in a complete shift of the hip-hop landscape, and the initial sign that an alien had just taken over our planet as we once knew it. From this point, Lil Wayne’s takeover of hip-hop from 2007 through the rest of the decade would be like nothing we had ever seen before or since. His swagger, his cadence, and the way we felt while watching him are all found in this freestyle.

If Rap City was as important to our rap nostalgia as we know it to be, Lil Wayne’s freestyle is our fondest memory.


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