Hearing Sway Calloway introduce his radio show's centerpiece, the "Five Fingers Of Death" challenge, is truly something to behold. Abruptly switching gears from his softer interview tone, he'll adopt an Ali-esque swagger and go off the top to hype up the segment, saying things like, "There ain't no smoke, there's no mirrors, this ain't Hollywood." It's theatrical, yes, but the challenge, which asks rappers to freestyle over five random (and often very eclectic) beats selected by DJ Wonder, is one of the most difficult in the industry. It's not surprising that most MCs nowadays opt out of it.
We've seen some good attempts recently, namely YG's from a few days back, but today, we're here to count down the all-time greats. Since the segment's inception in November 2011, many have tried, many have failed, and few have excelled. It's tough to judge freestyles, mainly because it's sometimes impossible to know whether the bars are pre-written or truly off-the-dome, but there are a few telltale signs that we're using as disqualifiers in this countdown. Number one: no reading bars off your phone (ruling out Meek Mill's otherwise pretty dope appearance). Number two: it's gotta be more than bars that appear in past or future songs (for example, Your Old Droog shot himself in the foot by rapping the entirety of his track "Porno For Pyros").
It was a struggle ranking these, so first we've got to shout out some honorable mentions. Childish Gambino came with some clearly spur-of-the-moment bars and was original as always (complete with a Scrooge McDuck mention), but he stumbled at times. Cassidy proved why he's earned a rep as one of the best battlers of his time, but he got repetitive at times and only went for under two minute total. Joey Badass killed it earlier this year, but those bars were clearly pre-written. The ten we've selected blow those others out of the water, whether they're well-known rappers with huge followings or under-the-radar battlers.
"You are now entering the Five Fingers Of Death..."
Tito Lopez
One of many rappers Dr. Dre took under his wing then quickly discarded in the years between 2001 and Compton, Mississippi's Tito Lopez was confronted with a wildly varied collection of beats and killed every single one. Hard to tell if this is or isn't written, but with the "Don't play yourself Sway" shout, some killer bars like "I dropped more projects than gentrification," and the domination of songs by Edward Sharpe & The Magnetic Zeros and Todd Rundgren, you've gotta give it to him.
Richmond, Cali's Locksmith has yet to break out, but as a lyricist, he's already top-notch. Some of this seems a bit too perfect to be freestyled, but there are a few moments that he gets candid, laughing and then recovering well with some bars about Sway. The clincher is how well he handles beat number three, which is a ridiculous drum cadence that anyone else would struggle with.
These days, we don't get to see Common freestyle that much, so it's always a treat. Here, he shows that he hasn't lost a step since his more rugged 90s days as Common Sense, getting a chance to test his skills when Sway adds the additional challenge of prompting him with random words every few bars. He was already going off the dome from the start, rapping exclusively about the present moment, but then things get taken up a notch. Com doesn't have the most intricate bars here, but he's clearly better than most at thinking on his feet. (The freestyling starts around 20:30.)
Prevail (of Swollen Members)
When Sway invited Swollen Members up to the show, only one member opted to take on the Five Fingers challenge, but Prevail proved he was more than capable going dolo. DJ Wonder does a great job of blending beats with the same tempo but utterly different styles, and even more astounding is that Prevail keeps up and changes his flows on a dime. He's the rare rapper who manages to include SAT words in his rhymes but is clearly freestyling, referencing specific characteristics of each track.
Pap is such a battle-tested freestyler that it's highly likely that he's got writtens for every type of beat, but watch this and tell me that he isn't impressive as fuck, regardless of any of that. He adjusts his flow effortlessly between BPMs, and only needs a split second before he launches into a mind-boggling double-time on top of Azealia Banks' "212." He even keeps going acapella, further cementing his greatness as a lyricist.
Logic
As far as technically sound performances go, Logic would be at the top of this list, but unfortunately, he leans a bit too heavily on material that would appear on his track "Soul Food" soon after this freestyle. That would be enough to disqualify him if he didn't rebound in the second half of this thing with some very clearly improvised lyrics. The fact that there's no obvious dip in quality is frankly crazy.
Lecrae
Much like Logic, Lecrae starts by leaning heavily on a few pre-writtens, but then transcends this by going off the dome for the last half. What's more, he goes for about four minutes, which is much longer than Logic lasted. Lecrae is more than just the most successful Christian rapper ever, he can also go toe-to-toe with anyone in the bars department.
Brother Ali
Ali's first verse comes from his track "Dreaming In Color," but all four of the next ones are spontaneous. From an "Azealia Banks-type beat" to Nirvana's acoustic version of "About A Girl," he kills it, capping it all off with his most powerful verse yet. Not that you need a gauge to tell how effectively he kills it, but seeing Murs wyling out in the background is certainly a nice touch.
Dizzee Rascal
UK grime legend Dizzee Rascal came up for the first time earlier this year, and instantly showed that he deserves to be recognized stateside as the lyrical genius his is. DJ Wonder kicks things off with two Future beats, then moves to some more old-school territory, all of which is out of character for Dizzee, who's more used to dance tempos, but that doesn't seem to matter. None of his lyrics appear on any tracks he's released, and his speed alone is jaw-dropping. Get on his level!
King Los
Sway hypes this one up to no end, revealing that he and DJ Wonder only chose beats by GOAT lyricists, and Los lives up to the challenge. He's the only guy other than Common on this list to accept Sway's random word generator challenge as well, and even with that additional hurdle, he blows the competition out of the water. He's simply the best in every category here: originality, endurance (dude goes for eight minutes straight!), and consistency. This is the high-water mark for freestyling in the past five years.