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The Winnie Coopers have their basis in the community — community groups to be exact. Charlie Thomson, who raps as the Educator, began performing when only 12 years old as part of a Gold Coast community group's outreach program. Although he was sidetracked by rock & roll in his teenage years, joining a band called Nagasaki, by 2002 hip-hop had called him back. With DJ Indelible he recorded a four-track EP, which, although it was never released, became the foundation of the debut Winnie Coopers album. That album, Being Different, was released independently in 2005 with help from DJ Webstar. They financed the album themselves and, with no way of getting the word out and selling copies, found themselves in debt.
The Educator, so named because of his day job teaching high school, was blessed a second time by a community group when he met fellow rapper Eloquence working at a youth center. The two were soon writing rhymes together while carpooling. With Eloquence sharing the microphone duties as well as playing the guitar, they had the basis for an actual band. They were joined by Young Tubs on bass, Bigbad on turntables, and Fingers Malone on drums just in time to win a competition to support Ugly Duckling at two of their sold-out Australian concerts.
Based on that exposure, they played the Big Day Out Festival in 2006 and supported several other big-name acts on tours of Australia, including De La Soul, the Beastie Boys, and Jurassic 5. After a delay, their second album, Worth the Weight, was released in 2008, featuring as its lead single a love song about food called "Eating Disorder," which featured Dizzy Dustin of their friends Ugly Duckling. The group, containing two former school captains and a member of the chess club as well as a teacher, naturally gravitated to geekier topics than are usual in the blokey, beer-soaked world of Australian hip-hop, which was only fitting for a group named after the nerd heartthrob of TV show The Wonder Years.