Andrew and Peter Cash have long individual musical histories, although they only came together musically in 1999 for the first time. They never played music together as children, but both are established figures in the Canadian music scene; Peter Cash was the principal songwriter for the Skydiggers, and Andrew Cash was a longtime solo artist who appeared in the bands L'Etranger and Ursula.

After ten years of touring, writing, and recording in these separate projects, the brothers decided to find out what sounds they could create if they joined musical forces. The result was 1999's Raceway. The first song that they recorded together, in 1997, was the title track on the album. "I remember going into the control room to hear what it sounded like," Andrew recalled. "We just looked at each other and said: 'Hey, this is going to work!'" The brothers' vocal harmonies on that first recording endeavor foreshadowed what was to come.

The Cash Brothers have earned critical accalaim and the respect of peers and fans alike with follow up albums How was Tomorrow (2001) and Brand New Night (2003).