Back in the mid-80s, Toronto was re-emerging as a musical hotbed with a special focus on a rebirth of the singer-songwriter tradition. The Cowboy Junkies and Blue Rodeo were in their formative stages. Andrew Cash, who had recently signed a solo deal with Island Records, had begun hosting a weekly songwriting showcase at the Spadina Hotel called Acoustic Meltdown, which obtained a cult following among music-lovers in the city. Future Skydiggers Josh Finlayson and Andy Maize were frequent guests at those shows. They had been friends since childhood, and separately had formed their own bands. Maize fronted Direktive 17, which toured around Southern Ontario. Finlayson played bass in The Ramblers, which had relocated for about two years to the UK chasing the tail end of punk’s glory years. By 1984, both bands had run their course, and the two teamed up to play and record as an acoustic duo under the name West Montrose. The simplicity and portability of the acoustic format was a reaction to their experience with the noise and circumstance of playing in rock bands. As they continued to write and record and occasionally appear on the Spadina stage, gradually the elements of a new group started to fall into place.
Drummer Wayne Stokes was an aspiring home studio purveyor who had done some recording with Finlayson and Maize. Bassist Ron Macey was a professional screen printer who was looking to a new career in music; he met the band through a want ad in a newspaper. Peter Cash, brother of the Spadina Hotel’s headliner, worked the door at the venue and an impressive tape of his formative songwriting efforts was slipped to the rest of the band.
When Andrew Cash decided to end his residency at the Spadina, he turned it over to the new musical collective, which had taken the enigmatic name Skydiggers. Some listeners initially likened the band to REM, but Finlayson says the roots of their sound and worldview ran deeper.