Kanye West at 20

We start off with the recent footage of Kanye at age 20, rapping with Cap 1 at what looks like a local event. A young Ye is already rocking sleeveless t-shirts and a (small) gold chain.

Bonus cut:
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;feature=player_embedded” target=”_blank”>Here‘s footage of Kanye, again in 1998, this time alongside Mase at the Jermaine Dupri birthday bash where he is introduced as an upcoming producer. More importantly, he can be seen rocking some seriously fresh glasses (Kanye footage is at the end of the video) [via Egotripland]

Fat Joe, Percee P and Eminem freestyling on the radio and in a toilet

You read that correctly. This gem of a video (pointed out to us by Illum Sphere a while back) includes classic footage of Fat Joe and Percee P kicking it and freestyling on the radio, followed by Percee throwing down with a fresh-faced Eminem in a toilet. Skip to 4:12 for the Em footage.

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Kendrick Lamar street cypher

Street cyphers have long been an MC’s true test, where bars are often spat acapella while the crowd cheers you on, or boos you out. In this video a young Kendrick Lamar shows that he’s got the skills to become one of the best. The Aftermath line is also pretty funny.

Tupac aged 19 in the studio and on the road

There’s vaults upon vaults of footage of Tupac Shakur at various stages of his career, but we’d never seen this studio and on the road footage of Tupac at 19. It shows him recording his song ‘It Ain’t Necessarily So’, featuring Shock G (for whom Tupac used to be a dancer) and freestyling, and by the looks of it the video ends on the set of the film Juice.

Bonus cut:
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;feature=player_embedded” target=”_blank”>Grainy as hell footage of Tupac spitting on the streets of his original hometown, New York City.

Snoop Dogg, Tha Dogg Pound and Dr. Dre freestyling in the studio

If you’ve ever wanted to see Dr. Dre play the melody from BDP’s ‘The Bridge Is Over’ on the piano while Snoop and Tha Dogg Pound beatbox and freestyle, ou’re in luck. It doesn’t get much more fly on the wall than this.

Kool Keith breakdancing as Jazzy Jay and Bambaataa spin

Many rappers from the late ’80s and early ’90s came up as breakdancers, and this video shows a young Kool Keith in his pre-Ultramagnetic days busting some dope moves. No rapping, but when you have that hat, stripey top and socks combo it’s hardly a loss.

Bonus cut:

More Keith breaking, this time for the Richers (Keith appears at the 2:30 mark).

Notorious BIG on the streets of New York in 1988

Perhaps one of the better known bits of ‘back in the days’ footage. One minute long but enough to see Biggie destroy his opponent, who walks away in shame at the end of the video. This was apparently the footage that inspired a similar scene in the Notorious movie.

Black Thought of The Roots freestyling on the streets

This short but solid footage of The Roots’ MC Black Thought shows him spitting some of his (soon to be) famous bars while a young Questlove provides the beatbox backing. Half way through Quest starts to throw him word cues, which again leads to rhymes that would become part of The Roots’ catalogue.

Mr. Lif, El-P and RJD2 in-store in 2002

Back in 2002 the Definitive Jux label pretty much ruled the indie rap roost on the East Coast. This in-store footage from Criminal Records sees a young Mr. Lif and El-P – with RJD2 providing the beats – spitting the sort of bars that would have had the backpacking audience running home to change their pants (we imagine).

ODB and RZA bum-rushing a talent show

If you’re going to crash the party at a talent show then you want to do it properly. No politeness, no ‘excuse me’, just grab the mic and shout like ODB before lacing the audience with curse words. Turns out not only was ODB a larger than life character, he could also rock a mean beatbox, with two microphones.