He began rapping at a very early age, around eight, and for a short while took the name "Angel Face Killer" because of his angelic face but fierce battling ability. During his time as a teenager Chester was very troublesome especially at school, rebelling against forms of authority imposed on him. Chester managed to channel his anger as a youth more constructivly in the form of battling and freestyling. He became very skilled at battling and earned himself a reptuation and is prolific in the British hip hop scene as a battler. He famously battled Common and defeated him, although he has been keen to play down the importance of this event, claiming that neither of them were on particularly good form that night.
Having proven himself in battling Chester has moved towards rap of more depth, the transition most prevalent with the release of the Music From The Corner series. Typically referenced areas within Chester's music are now astronomy and markedly a return to life at one with nature, although many tracks still contain battle orientated elements. In 2006 Chester challenged Wordsmith to battle after a recording of Wordsmith attacking Chester surfaced on myspace. Chester wrote a retaliation track, "The Bitches", which was first aired on Shortee Blitz and Big Ted's hiphop show on Kiss 100.
The track is notable for containing a recording of a phone conversation between Chester and Wordsmith that shows Wordsmith backing down and all but apologising for his track. In early 2007 Wordsmith and Chester ended their fued. There are rumours that they may do a track together. Read more on Last.fm.
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