As the 1980s were drawing to a close, childhood friends singer Andy Maize and guitarist Josh Finlayson saw their duo act West Montrose, which had done the Toronto area bar circuit for a couple of years, was running its course. They’d both been in their own groups prior to that – Maize in Direktive 17 and Finlayson in The Ramblers, which had relocated at one point to the UK at the tail end of the British punk movement. With the ambition of writing their own music seeming unlikely while stuck in a duo, they added rhythm guitarist Peter Cash and drummer Wayne Stokes. Ron Macey came on board on bass soon after, after answering a newspaper ad.
Thanks in part to Andrew Cash (Peter’s older brother) and him hosting a weekly songwriting showcase, they got a steady gig at the Spadina Hotel. They settled on the name Skydiggers, as suggested by Andrew, and a name he’d once considered for his own backing group. From the Spadina they branched out and played the rest of the Queen Street circuit, and by the summer of ’89 their demos they’d sent out had gotten the attention of several record label executives.
They became the first Canadian act to sign with California-based Enigma Records that year, who released their eponymous debut album in the summer of 1990. Recorded at Phase One Studios in Toronto throughout the previous fall with producer Andrew Scarth, the album was heralded by the critics for its rock and roots fusion. It produced four singles over the next nine months – “Monday Morning,” “We Don’t Talk Much Anymore,” “Maybe It’s Just Not Good Enough,” and the gentle “I Will Give You Everything,” which peaked at #24 on the Canadian adult contemporary chart, and #38 on the pop singles chart. But the label’s financial woes equalled a lack of proper promotion of the album, and the label declared bankruptcy before the end of ’91.
A core of Enigma’s Canadian staff, namely Mark Smith and Derrick Ross, created FRE Records in ’92, releasing the band’s sophomore album, RESTLESS that August. They recruited Mike Sloski and Steve Pitkin to fill in as drummers after Stokes left the band, and recorded in Toronto and Daniel Lanois’ Hamilton studio with producer John Oliviera. The album quickly climbed to #34 on the charts on the back of the singles “A Penny More” and “Feel You Closer.” Both songs spent time in the top 40, and with new full-time drummer Joel Anderson, they embarked on an ambitious Canadian tour. As an added push, Capitol Records, who was the distributor for both Engima and FRE, also got on board, releasing both albums internationally.
Next up was JUST OVER THIS MOUNTAIN in ’93, and again Cash was the predominant songwriter, and for the first time the band produced the album itself. Once recording was finished, Anderson left the group and was replaced behind the drumkit by Peter von Althen. None of the three singles – the title track, “I’m Wondering,” or “80 Odd Hours” cracked the top 40 on either the pop or the adult contemporary chart. But still the album made its way to #42, helping earn the band a Juno that year for most promising group.
They contributed a cover of “Mr. Soul” to BORROWED TUNES: A TRIBUTE TO NEIL YOUNG in ’94, and after signing with Warner Canada, released the ROAD RADIO album a year later. Stripped down and recorded for the most part live off-the-floor at The Lighthouse Theatre in Port Dover, Ontario, things were looking up when the lead-off single “What Do You See?” made its way to #22 on the AC chart. “It’s a Pity” and “You’ve Got a Lot of Nerve” also received alot of buzz. But while they were on tour that fall, they found themselves without a label for the second time, when FRE closed its doors. This meant that not only was promotion for the new album cut short, but the back catalogue was no longer available either. Although the band tried to win back the master tapes, they were unsuccessful. Making matters worse was the fact that once the road bus was parked, Cash and Von Althen both left the group.
They signed with DROG Records, and with new guitarist Paul MacLeod and session drummers, released DESMOND’S HIP CITY in 1997. Self-produced, a bevy of guest musicians that included Sarah Harmer and Jim Cuddy was included. Since it had been partially defined to this point by Cash and Maize’s vocal harmonies, the record took on a more modern rock approach and paid less attention to their roots rock sound. “Dear Henry” was the only single, but failed to chart. Other tracks like the title song were driven by keyboards, while “November in Ontario” and “The Shape of Things To Come” had a harder edge than anything previously released. They set out on the road for the better part of the next year, which included an opening slots on Sarah Harmer’s and Blue Rodeo‘s Canadian tours.
Still unable to secure the rights to the master tapes for the RESTLESS album seven years earlier, their next project in ’99 was to re-record the bulk of the album, dubbing it STILL RESTLESS: THE LOST TAPES. Made up primarily of old rehearsal recordings, it also included four tracks originally scrapped from the original album – “It’s Alright,” “Joanne,” “All Alone,” and “Good King Wenceslas.”
They released their first live album, THERE AND BACK, in 2000, the bulk of which was recorded at Toronto’s Horseshoe Tavern the previous December, while three tracks were taken from a 1998 show at Edmonton’s Sidetrack Cafe. Along with a collection of the band’s most requested songs, it also included their version of Jesse Winchester’s “Biloxi,” a live version of their new song “Those Memories,” and the new studio track “Will You Ride Wide Open.”
After launching MapleMusic Recordings (future home for Colin James, Chantal Kreviazuk, Radiohead, The Rankins, and Cyndi Lauper), they followed it up with a limited edition release of their new album, BITTERSWEET HARMONY in 2002, which came in a different jacket than when it was released a second time – this time to the masses the following spring. Sparked by the lead-off “Anything For You” as the single, initial response was favourable, although it, like the album, failed to chart. Other critics favourites included “Horseshoe Bay,” “Jane’s Gone,” and the reflective “All of Our Dreaming” (not included in the original release).
2006 was a year of side projects for the band. Finlayson and Maize released their album DARK HOLLOW that year under the guise of, oddly enough, Finlayson/Maize. And although Peter Cash had left the group over a decade earlier, he and his brother Andrew were still close friends with the group. The band teamed up with The Cash Brothers that same year to release an acoustic album, entitled appropriately enough SKYDIGGERS/CASH BROTHERS, featuring half a dozen new tracks from each group.
Next up was CITY OF SIRENS in 2008, marking the band’s 20th anniversary, and their first project for their new label, Latent Recordings (founded by Cowboy Junkies). The album was heralded for its return to a bluesy roots/rock feel in songs like “Hasty Mart,” “Everybody Wants All,” “When You Walk By,” and the title track. The band’s first compilation, THE TRUTH ABOUT US: A 20 YEAR RETROSPECTIVE followed a year later.
In 2010 Maize recorded his critically-acclaimed solo album called A HISTORY OF FORGETTING, while Finlayson lent a hand on the project. Around the same time he was also providing his talents to Cowboy Junkies, Tragically Hip‘s Gordon Downie for his two albums, and Mary Gauthier.
They got back together in 2012 for NORTHERN SHORE, argued by some as their most diverse recording ever. Produced by Saam Hashemi and recorded predominantly at Toronto’s Woodshed Studio (Blue Rodeo‘s facility) and Tragically Hip‘s Bathouse Recording Studio in Kingston, the album was 15 tracks that ranged from the acoustically-driven “The Herd” to the progressive title track, which was the first single. Many of the songs were older material that for one reason or another had been shelved during previous recording sessions, as well as covers of The Cash Brothers’ “Barely Made It Through” from the 2006 split album, and Andrew Cash‘s “Wake Up Little Darlin’.”