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.
“We were always compared to REM, but really it was more a case of having the same influences – the Beatles and the Byrds. The common thing would be the layering of voices. Also, Joe Klein’s book about Woody Guthrie (Woody Guthrie: A Life) was passed around between us, and it made an impression. Woody’s life and work embodied a lot of the ethos and the ethics of punk music. He was very direct and independent and stood for something about the individual and championing people and causes.”
Adds bassist Macey: “For the longest time it was like a skiffle band, very rhythmic and percussive. Essentially, it is two acoustic guitars, four voices and drum and bass. It had to go somewhere from there.”
The sound developed at an impressive rate, thanks to the discipline and work ethic the weekly showcase placed on the band. New songs, new covers and a sound that grew to include electric instruments developed in the hothouse atmosphere of rehearsals, songwriting sessions and live performances. The buzz about those early shows reached Mark Smith and Derrick Ross of Enigma Records and they snagged the band for their eponymous debut in 1990.
Although the initial single was the rollicking “Monday Morning,” it was the gentle ballad “I Will Give You Everything” which made the group’s reputation and garnered substantial play on both radio and music television. Their sophomore effort, Restless, saw them recording at Daniel Lanois’ fabled Grant Avenue studio in Hamilton, Ontario, and the sophistication of their recordings grew exponentially. In 1993, they issued the languid, atmospheric Just Over This Mountain, and in 1997 they jumped to Warner for Road Radio, which was recorded mostly live-off-the-floor at the Lighthouse Theatre in Port Dover, Ontario.
Stokes departed after their sophomore release, Restless. Peter Cash left in 1996 after Road Radio. (Cash went on to record and tour with brother Andrew, and in 2005, both would collaborate again with the group on the disc Skydiggers/Cash Brothers). The departures and drafting of new players have fueled the evolution of the group’s sound. Desmond’s Hip City saw them toying with sampling and looping and dueting with Sarah Harmer, Bittersweet Harmony swung back towards the guitar-based pop influences of their early days and more recently City of Sirens was fortified with the presence of keyboardist Michael Johnston, who has injected novel textures into the Skydiggers’ sound.
“We’ve played with other people, other people have come into this circle and played with us. They’ve put their stamp on our music. But on the other hand, I think we recognize there is something consistent and something we all value that is threaded through all our records,” says Finlayson.
“If you manage to spend this much time making music together, you will find there’s some chemistry, some magic that makes it work,” adds Maize. “We don’t question where it comes from, but this record is our chance to celebrate the fact that we’ve been part of something pretty special.”