Vintage Videos Of Your Favorite Rappers Freestyling Before They Were Famous

Vintage Videos Of Your Favorite Rappers Freestyling Before They Were Famous


June 15th, 2015


Are you an aspiring artist struggling to find your niche? Don’t sweat the uphill climb. Everyone starts somewhere, and very few have an easy path to success. To reinforce that grind mentality, we’ve dug up videos from many of today’s biggest rappers, freestyling for fame before they were stars.

You never know, 2020’s biggest rapper might already be dropping that hotness on YouTube.

1. Big Boi Gets Busy In High School

This clip from 1993 shows a 17-year-old Big Boi practicing raps for what appears to be a school project and is a pure gem. Young Luscious Left Foot’s charisma is already on point and seeing him rubbing off on his peers is rather charming. Big and Dre would end up releasing their debut album within a year of this footage.

2. Kendrick Lamar Kicks Bars In The Projects

Seeing Kendrick casually battling fellow MCs in this vintage clip is great for numerous reasons. First, he’s arguably the most sought after rapper right now and watching him on the game’s entry levels is far out. More importantly, seeing Dot vying for position amongst crowds of pure rap enthusiasts in the infamous Nickerson Garden projects, provides a sense of hope. Notice the vintage Top Dawg gear, too.

3. Kanye Freestyles At Fat Beats

If this video of Kanye West’s impressive freestyles at Fat Beats from August of 1996 doesn’t blow your mind in itself, consider the fact Tupac was still alive when it was recorded. Yeezy earned everything he has. Never forget that.

4. Big Sean Gets Gamed In High School Freestyle Circle

Big Sean might be one of the game’s heaviest hitters right now, but watch this 2006 clip of the Detroit rapper in a high school versus high school freestyle battle, and you’ll see Sean Don get one-upped by a killer one-liner. He attempts to clap back, but a wannabe Mr. Belding ends up breaking up the circle. Of course.

5. Meek Mill With Ill Rhymes & Nappy Braids

Although his energy is a bit toned down, there isn’t too much different with Meek Mill’s skill from this clip of him from 2004 to now, over a decade later. The hunger is there. The content is there. The undercover melodies are there. The stylist, however, clearly was not.

6. Drake Plotting Greatness In Home Studio

Back in 2006, Drake’s name wasn’t exactly popping to the masses, but that doesn’t mean he was light on the confidence. In this clip from almost a decade ago, the OVO rapper speaks to his inevitable success and freestyles about all the delicacies his life already includes. This guy hasn’t had a bad day in his life.

7. Jay Z With Big Daddy Kane On Rap City

These days, Jay Z gets on television whenever he wants, in whatever capacity he sees fit. But in early 1991, the Marcy titan didn’t have the same pull and took advantage of any chance to rhyme for the masses he could. So, when he was asked to freestyle as a guest of Big Daddy Kane on Rap City and host Hans Dobson didn’t even mention his name, the giddy Jigga didn’t sweat a thing and proceeded to kick his wicked flows anyway. How the times have changed.

8. Mos Def Gets Busy On Power Move Radio

There’s lots of vintage vibes in this well-kept clip from 1992 of Mos Def participating in group freestyles for a cause on Power Move radio show on CKLN Toronto. Mr. Bey hasn’t aged a day.

9. Chance The Rapper Kicks Bars In Middle School

Considering Chance the Rapper recently released one of the most heralded projects in all of music last month, we’re wondering what he thinks when watching this clip of him freestyling off the dome from 2009, back when he was in either eighth or ninth grade. Probably that’s he’s lost a bit of baby fat.

10. Joey Bada$$ Delivers Life Changing Bars

In this clip of young Joey Bad, the Brooklyn rapper — then known as JayOhVee — is seen at the age of 15 freestyling with friends. As you can hear, he’s clearly been sick from the start. Not surprisingly, this is supposedly the clip that got the Pro Era leader signed with Jonny Shipes’ Cinematic Music Group, who proceeded to help kick the young spitter’s career into full swing.

11. J. Cole Sets Sights High In A Capella Freestyle

Somehow J. Cole got into New York’s famous Baseline Studio back in 2006. Feeling the legendary vibes, the future chart topper stood in front of his would be boss’s plaques and laid down a capella bars on how he’d eventually achieve the same success as his idols. Talk about calling your shot. Plus, you’ve got to love his “Produce for Jay Z or Die Tryin” tee.

12. Mac Miller Spazzes In Lunch Room Circle

Before Mac Miller became an independent superstar, he was originally known as EZ Mac and had no problem spitting in circles in the cafeteria. It’s obvious the Pittsburgh MC has always led the pack, when you see the baby faced Mac effortlessly flow from the dome over table top drums in this vintage clip, while teenage crowds clammer for more.

13. Nicki Minaj Gets Gutter On ‘The Come Up’

As part of her spot on Jordan Towers’ The Come Up DVD series from 2008, a budding Nicki Minaj can be seen acting ornery as you’ve ever heard her. She’s calling out names and flaunting stacks of money in a stairwell, with a New York accent thicker than her current ass. Where the hell did this new Barbie chick come from, again?

14. Eminem’s Early Battles

Most people know Eminem grew up, sharpening his lyrical swords at freestyle battles in Detroit and eventually in Los Angeles, where he would eventually be discovered by Dr. Dre. This highlight clip of some of those vintage battles is a strong reminder Slim has always been the illest in the room.

15. Ludacris Kicks Fast Flows From Home

Watch this quick clip from VH1’s Behind The Music on the ATL legend and you’ll see how Ludacris used to have a Twista-esque fast flow, before having the best diction in Hip-Hop. Stand up!

16. 50 Cent Incites Awe From Consequence & Noreaga

Remember when rapping was 50 Cent’s top priority? Seems like a while ago. That’s why this clip of a young, baby-faced G-Unit leader spitting alongside Consequence, Noreaga and others is so choice. Not only is the hunger there, his bars actually seem to be off the top. These days, Fif isn’t doing sh*t for free, let alone actually freestyling.

17. Rick Ross Rapping Without A Beard

Can you even imagine Rick Ross without his patented beard? If not, here’s video of him rapping along to what appears to be a Trick Daddy song in 1998, using lots of hand movements and sans his famous facial hair. Oh, Gunplay is on stage, too, and looks exactly the same.

18. Notorious B.I.G. Freestlyes In Bed Stuy Streets

If you’ve never seen this clip of a teenage Biggie freestyling in his neighborhood block, it still might look familiar, having been recreated in Notorious. For a 17-year-old, dude had the deepest voice… maybe of all time. Long live the King of New York.

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