Skydiggers are a Canadian alternative country/indie rock band from Toronto, Ontario.
Formed in 1987 by singer Andy Maize and guitarist Josh Finlayson, the band soon added Peter Cash, Wayne Stokes and bassist Ron Macey to their lineup. They quickly became a regular house band at Toronto's Spadina Hotel, often playing with Cash's brother, singer/songwriter Andrew Cash.
In 1989, the band became the first Canadian signing to Enigma Records. Their self-titled debut album was released on Enigma the following year, and spawned the singles "Monday Morning" and "I Will Give You Everything". However, the label soon went bankrupt, and the album was never properly promoted.
Some of Enigma's Canadian staff created FRE Records in 1992, and released the band's second (and most popular) album, Restless, that year. At the same time, Stokes left the band. Drummers Mike Sloski and Steve Pitken filled in on drums until the band recruited Joel Anderson as its new permanent drummer. "A Penny More", the lead single from Restless, became the band's biggest hit.