From the lunchroom and lockers to the playground and parties, the cypher is where some of the greatest rappers of all time were made. The internet may have changed the game, but these breeding grounds will forever be an important place for MCs to hone their skills, sharpen their delivery and develop the confidence to perform in front of a crowd. Plus, a generation of kids can bang out the beat to Clipse’s “Grindin’” by heart.
Digging up old freestyles from famous rappers can be a fascinating task. They give you a glimpse at what these artists were like when they were younger, who some of their earliest influences were and how they’ve grown as both artists and people—or sometimes it’s just funny watching your favorite rappers spit rhymes before they had any idea they’d be famous. Who isn't completely embarrassed by their 15-year-old selves?
For these very reasons, we decided to scour the internet and dig up the earliest freestyles we could find from 20 of our favorite rappers.
A$AP Rocky was heavily influenced by Kid Cudi before Yams put him onto the syrupy sounds of Houston and Memphis, but whatever musical—or hair—style he’s adopted, Pretty Flacko can rap; he’s named after the great Rakim, after all. Just peep this video of a young Rocky stepping into an otherwise underwhelming cypher and attacking it with the intensity of a Dipset stan who’d sold drugs and lived in shelters across Harlem and the Bronx. Even those dudes mean muggin’ in the background couldn’t help but turn around and take notice.
It was a freestyle at a local Detroit radio station where Big Sean introduced himself to Kanye West—and subsequently scored a G.O.O.D. Music deal—but it was on Canada’s MuchOnDemand, in 2002, where a 14-year-old Sean Anderson introduced himself to the world for the first time. Two things haven’t changed since then: Sean’s remarkable ability to foretell his own future (15 years after rocking that Roc-A-Fella tee on TV, he’d be gifted his own Roc-A-Fella chain by Hov himself). And his voice.
Chance The Rapper
Your first thought watching this video might be, “HOLY SHIT CHANCE REALLY GREW INTO HIS FACIAL STRUCTURE.” The second is how even a 16-year-old chubby-cheeked Chano had a firm grasp of his identity—and the self-depreciating humor to match: “I don’t have a gun, I’m a bitch ass n*gga / Like, I ain’t never ever pulled no trigger / I ain’t sell no drugs and I ain’t trying to be a thug / But if it comes down to the paper, I write better than you.” That he did.
The first video evidence of Childish Gambino rapping is exactly how you pictured it: a young Donald Glover, rocking a skateboarding tee, freestyling in a room full of white kids while a Jimmy Page look-alike plays AC/DC’s “Back In Black” (oh, the irony) on an electric guitar. You know why you don’t see more electric guitars in cyphers? Because you can’t hear a fucking word anyone’s saying (that’s a lie: I heard Donald say, “I make girls’ balls turn blue” and… yeah). Donald isn’t the only rapper in this video who eventually found his voice; Chaz Kangas, the white dude he’s battling, is currently an on-air host for Go 95.3 and Go 96.3 in Minnesota. He even wrote a backstory behind the video.
Eminem’s battle rapping days were immortalized in the box office smash 8 Mile, but the genuine article makes for equally thrilling cinema. Here’s a young Marshall Mathers at the famed Hip-Hop Shop in Detroit in February ‘96, battling—and beating—his D12 bandmate Kuniva. Loud Records CEO Steve Rifkind may have passed on signing Eminem around this time, but it was Slim Shady’s performance at the Rap Olympics in LA the following year that won Interscope boss Jimmy Iovine over. The rest is history.
And now for the most embarrassing video on this list (Cole, if you’re reading this, I’m sorry). Everything about this clip is almost unrecognizable from the J. Cole we know today: the buzz cut, the baggy clothes, the aggressive New York flow, even the name (Therapist). But hey, you don’t become a global rap star who goes double Platinum with no features without going through a typing-out-your-battle-raps-on-Canibus-message-boards phase.
A full six years before he released Reasonable Doubt, JAY-Z Jaÿ-Z delivered his first televised freestyle on BET’s Rap City—who were a long way from reaching their own prime—in 1990. If his babyface and goofy smile don’t already belong in a time capsule, Hov’s “funky freestyle” definitely does. I’m just gliddity glad I was born two years after this.
As the story goes on “Last Call,” a young Kanye West packed up his shit, dodged eviction in Chicago and moved to New Jersey in 2001 to get things poppin’ the way they should have been (safe to say the gamble paid off). But five years before that, an even younger Kanye was making trips to the Tri-state area to test his mettle. DJ Eclipse unearthed this rare artifact from August ’96, which finds a 19-year-old Ye—who only had the backpack, not the Benz—freestyling at the famed Fat Beats store (RIP) in NYC. The first 12 seconds of this clip epitomizes Kanye’s early career: a seemingly goofy, awkward kid in a polo who could transform into an ultra confident rapper at the drop of a beat.
Kendrick Lamar and Nas have a lot in common, not least the good-kid-in-a-maad-city approach on their respective debut albums. But while a young Nas was “too scared to grab the mics in the parks,” K. Dot clearly had zero hesitation. Even while surrounded by Bloods in Watts’ Nickerson Gardens—the home of Jay Rock and the same projects TDE returns to every Christmas—a teenage Kendrick, standing no taller than 5'5", was rapping like a giant: “I’m so far ahead of my time, I got people five years from now pressing rewind.” No wonder the whole city got behind him.
Kevin Abstract, who as a teenager looked like Lupe Fiasco and rapped like Troy Barnes, got off to an awkward start in his middle school battle rap career. “Your momma always call me on my phone / Asking me…for some sex,” he rapped with the self-assurance of a kid who was at least 10 years away from fulfilling such a claim. Thankfully, young Kevin managed to pull it back and collect the W. I’m just disappointed no one caught the Ma$e line.
Before A Kid Named Cudi, signing to Kanye West and a curious career of game-changing highs and soul-crushing lows (not including Speedin’ Bullet 2 Heaven), Scott Mescudi was a lonely stoner living in New York just trying to get out his dreams. If there’s one thing that’s remained consistent throughout Cudi’s tumultuous timeline, though, it’s his ability to harmonize the hell out of a beat, as evidenced in this clip from a session with producer 88-Keys in early 2008. “After recording ‘Waisting My Minutes’ for my upcoming mixtape Adam’s Case Files: The Mixtape, I just threw on some old-ass beats I had laying around for a couple of yurrs [sic] (literally) and he just went off,” 88-Keys explains. “He was killin’ it for a while until I realized, ‘Hey… I should tape this sh*t,’ thus proving my genius.” Releasing it as a song would have been an even smarter move, though.
Lil Uzi Vert
Lil Uzi Vert may refuse to rap over DJ Premier beats, but he had no problem jumping on an Ol’ Dirty Bastard classic back in 2013. The young Philly rapper doesn’t immediately strike you as a future star on this posse cut from Diamond Cuts, who was actually the first DJ to play Uzi’s music on the radio, but his switch-up in style clearly paid off. Who knew that so-called mumble rappers can actually rap?
I present to you a teenage Mac Miller Easy Mac, rapping like Big L, smoking a square like El-P and wearing a fitted like T.I. I swear the cap’s vertical by the end of the video.
Long before his deal with MMG, relationship with Nicki Minaj and beef with Drake, Meek Mill(z) was making a name for himself as a formidable battle rapper in the streets of Philly. Even at 16 (not 13, like the video claims), Meek was channeling a chaotic childhood into bars that transcended his tender age, both in gritty content and ferocious delivery. Which only makes his loss against Drake, a guy who at the same age was appearing in Degrassi, all the more baffling.
It may look like this video was filmed on a Game Boy Advance, but apparently, it dates back to 2011, somewhere in between Migos first forming a group and dropping their breakout hit, “Versace.” Don’t let the poor quality of the video dampen the joy of watching Offset and Quavo, mouths full of gold and hearts full of hope, freestyle outside a house party, though. Unfortunately, Takeoff is nowhere to be seen—not for the first time.
Mos Def made his rapping debut as part of Urban Thermo Dynamics back in 1994—four years before the release of Mos Def & Talib Kweli are Black Star—but there’s evidence that dates back even earlier in Andrew Munger’s documentary, Make Some Noise. Focused on Toronto’s burgeoning hip-hop scene, the film captures a fresh-faced Dante Smith kicking mad grammar on DJ X’s Power Move radio show on CKLN-FM in ‘92. If you’re wondering what a young Brooklyn kid like Mos is doing in a documentary on Toronto hip-hop, allow Munger to explain: “At the Masterplan or the Power Move show you’d just have people show up—friends, friends of friends. There was a guy who had a clothing store [called] Hundred Miles…Garie…he brought his buddies from Brooklyn. I just thought [this rapper] was really good, and later it turns out that that’s Mos Def.”
When Nicki Minaj recorded this freestyle over Terror Squad’s “Yeah Yeah Yeah,” the thought of beefing with Remy Ma—or swapping Brooklyn label Dirty Money for Lil Wayne’s Young Money—probably felt further away than pink wigs and Europop songs. If “Moment 4 Life” was her Cinderella moment, this video feels like Nicki before being visited by the Fairy Godmother. Glass slipper or no, she’s always been able to rap her ass off.
The Notorious B.I.G.
The most-watched video on this list (at 6,854,247 views and counting) and arguably the best; Biggie was bulldozing bums with his bars before he was legally allowed anywhere near a bar. Even in the year 1989, Christopher Wallace was rapping like it was '94.
Skyzoo is an incredibly talented, if not sorely underrated, a lyricist who’s been spitting fire since long before projects like Cloud 9: The 3 Day High. In 2002, a then-unknown Sky appeared on 106 & Park’s Freestyle Friday competition and faced off against reigning champ Jin. Despite a close contest, Jin remained undefeated and went on to join DMX’s Ruff Ryders crew (he even had an admittedly amazing song with Kanye West), but 15 years later, things haven’t worked out too badly for Skyzoo either.
Tyler, The Creator
Only real Odd Future stans know about bloxhead. One of the first videos uploaded to Tyler, The Creator's old YouTube channel, this “Secret Garden” freestyle finds a 16-year-old Tyler - BAPE, Kanye West and Casey Veggies' Customized Greatly over a self-produced beat that sounds like an early draft of Bastard. Of course, there’s plenty of lines about “herpes,” “sucking dicks” and “fucking black dykes,” too. How far the Flower Boy has come.