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Wu Tang Clan fans are familiar with Shyheim when he was known as The Rugged Child, the youngest affiliate of the legendary hip hop collective. 

He made his debut in 1995 with Shyheim a/k/a the Rugged Child and an appearance on Big Daddy Kane’s “Show -n- Prove” alongside Old Dirty Bastard and a young Jay-Z. The Lost Generation followed, and by 1999 Shyheim released Manchild and was all grown up. The Greatest Story Never Told hit in 2005 and Shyheim has been on the mixtape grind ever since. He is currently getting much attention from his song and video for “Fat Boy”, a diss against Wu Tang’s Raekwon. It seems Rae shut Shyheim down when he was trying to get a DVD drop from P. Diddy backstage at a recent Wu tang show. And we all know that disrespecting an MC ain’t a good move, even if you are a legend.

In his Freestyle 101 session, Shyheim discusses the beef with Rae, his relationship with Wu Tang, and the hip hop scene in Staten Island. He even brought his cousin Guy (a.k.a. Illy Ale) along to Play Studios in Manhattan and the duo tag-teamed rapped about what kind of videogame they’d make over a chill Messiaz beat. Shy plays the man on the street in the big city, while Illy Ale plays the role of death as it sweeps through the streets. Life as a videogame…an interesting and unique approach.

This edition of Freestyle 101 is our first from what we’re calling The New York Sessions, a recent week-long trip to the Big Apple where we shot just about every known rapper you can think of, including Fat Joe, Sheek Louch, Ice-T, M.O.P., Mob Deep, Heltah Skeltah, Buckshot, Immortal Technique, Thirstin Howl III, Shabaam Sahdeeq, Ali Vegas, Hell-Razah, Shabazz the Disciple, Big Noyd, Teflon, Smooth da Hustler and more. Yup, it’s about to get real hood up in this b*tch! Check out the behind the scenes photos here.

Next week is Prodigy of Mobb Deep, shot about a week before his 3 ½ year prison sentence, so hit us up at 3 p.m. EST on Tuesday, Feb. 19th. In fact, we are also posting an exclusive interview with prodigy here tomorrow where he discuss his arrest and how he believes New York police tried to use him to set-up labelmate 50 Cent.

Visit us on MySpace, watch past episodes, rant in the Forums or check out some freestyles from other Wu Tang affiliates like Killah Priest and Prodigal Sunn, or fellow New York MCs Sean Price, Papoose, Termanology, Joell Ortiz, Cormega, Guru and Trife da God.