Greg Greenway was a promising high school and college basketball player when he became aware of the racial injustices experienced by his Black teammates. The experience inspired Greenway to write his first songs. In the more than two decades since, Greenway has continued to use his songwriting as a vehicle for sharing his humanistic views. On his 1992 debut album, A Road Worth Walking Down, Greenway sang of freedom during "Free At Last," inspired by the imprisonment of Nelson Mandela, and the title track. On his second album, Singing for the Landlord, released in 1995, he sang of Native American rights ("Ghost Dance"), the horror of a drive-by shooting ("She's Just Gone") and the depression of poverty ("Crack in the Wall").
Although Greenway's earliest acclaim came for his athletic abilities, he turned his attention to music after visiting Massachusetts during his senior year at William & Mary College in Williamsburg, Virginia. Walking through Harvard Square in Cambridge, he was inspired by the street performers and the singer-songwriters that he heard at the folk music coffeehouse Passims. Following his graduation, he returned to Massachusetts and formed an acoustic-based band. Although the group played throughout New England as the opening act for Livingston Taylor, Greenway became frustrated after a second guitarist was added. Leaving the band, Greenway formed Trace of Red, a cover band that specialized in interpreting songs by the Who and the Police. After playing with the band for three years, Greenway elected to return to acoustic music and, with bassist Doug Wrey, formed a duo in 1981. While they've occasionally expanded into a larger group, the duo's acoustic sound has remained consistent. Although Greenway had his greatest success with his novelty tune, "Massachusetts," which lampooned the poor driving of the state's residents, he's continued to make a lasting mark with his rhythmic songs of freedom and justice.
Following his marriage to longtime girlfriend Audrey in September 1996, Greenway moved to Massachusetts' Cape Cod.