The oldest of three children, Cunningham played harmonica at the age of five in the Grand Lee Old Age Pensioner Harmonica Band. Although he tried his hand at accordion and piano, he found his natural musical voice when a grandmother presented him a fiddle shortly before his eighth birthday. Leaving school and home at the age of 14, he spent several years living in rundown apartments in Edinburgh. A turning point came when he met Gordon Jones and Bob Thomas, musicians who managed the Triangle Folk Club. Moving into their communal apartment without bathrooms or heat, Cunningham joined them in forming a band, Silly Wizard. After playing several local gigs, the band accepted an extended engagement in Liverpool, England, writing music and performing in plays at the Everyman Theater. Returning to Scotland, the group added Cunningham's younger brother, Phil, on accordion, as well as traditional singer Madeline Taylor. Although they recorded an album for Transatlantic Records, the album has never been released.
After releasing a self-titled album in 1972, Silly Wizard went through personnel changes, with Taylor being replaced by Andy Stewart and bassist Martin Hadden of the recently disbanded group Puddock's Well. Following the recording of Silly Wizard's second album, Caledonia's Hardy Sons, Bob Thomas left the band, and the group continued as a five-piece unit. Silly Wizard's first tour of the United States included a pivotal appearance at the Philadelphia Folk Festival. Cunningham emigrated to America shortly afterwards in 1980. Although his place in Silly Wizard was filled temporarily by fiddler Dougie McLean, he played on their last recording, A Glint of Silver, in 1986, and joined them for their farewell tour two years later.
Cunningham continued to work periodically with his brother; in addition to recording an album as a duo, Against the Storm, they joined with siblings Triona NiDomhnaill and Michael O'Domhnaill of the Bothy Band to form Relativity in the early 1980s. Cunningham also worked with NiDomhnaill and O'Domhnaill in the new age Celtic band Relativity. Sadly, Cunningham died of a heart attack in December 2003. He was 46. ~ Craig Harris, Rovi