Matthews and McDonald got their start as The Renegades, recording as teenagers for Jamaican labels like Studio One and Bob Marley's Tuff Gong imprint. A name change followed the addition of members Rudolph "Garth" Dennis (who later founded Black Uhuru) and George "Buddy" Haye. The band's self-titled debut album is regarded as a classic. Many listeners remarked on how similar Matthews' reedy vocals were to Marley's, especially after Wailing Souls hit #1 on the Jamaican charts with their 1976 remake of "Back Out With It." By then, the group had enough clout to start its own label, Massive. A second proper album took years to emerge, but it proved worth the wait. Released on Island Records as Wild Suspense, it featured backing by Channel One house band The Revolutionaries and contained big hits like "Bredda Gravalicious." While some stars of roots reggae's heyday had a difficult time making the transition when dancehall became ascendant during the 1980s, Wailing Souls survived and prospered on a series of hits produced by Henry "Junjo" Lawes. They continued to crank out strong albums into the 1990s, recording for everyone from Columbia Records to smaller labels. In 1998 the group collaborated with members of Sublime on an album of reggae tinged '60s covers called Psychedelic Souls.

That the band has paid attention to recent musical trends is evident from the sleek, pumping pulse of the single "The Underdog," yet Matthews' urgent vocals and the group's trademark harmonies, which converge during a soaring chorus, root the tune firmly in Wailing Souls' proud, decades-long tradition.