The band was formed by Michelle McAdorey and Greg Keelor of Blue Rodeo in 1988, who were also in a romantic relationship. They had met in the late 1970s, and McAdorey had later appeared in the music video for Blue Rodeo's song Try. The two could not agree on a name for the band, originally selecting Giant Tambourine. McAdorey stated that they eventually settled on Crash Vegas by "bouncing words around", a name she liked for its "abrasive vividness". Jocelyne Lanois joined the band as bassist, and shortly after Ambrose Pottie joined as drummer. It was one of the early acts to emerge from the vibrant Queen Street West music scene that developed in downtown Toronto beginning in the mid 1980s. 

In July 1990, the band released its debut album Red Earth.Music critic Michael Fischer stated that the band was similar to the Cowboy Junkies "without the allusive angst",and a Knight-Ridder review stated Crash Vegas to be "an awake version" of Cowboy Junkies. The latter also described the band's sound as a combination of country music, pop music, and English folk rock 

Crash Vegas signed a new deal with London/Polygram in 1992. Darren Watson replaced Lanois for the band's second album, Stone,which also included contributions from John Porter and Butch Vig. Recorded in Los Angeles, the album was more energetic than Red Earth, though it also had a "bleakness" resulting from the dissolution of McAdorey's romantic relationship with Keelor. 

The song September Morning was a tribute song to Gram Parsons, a country rock pioneer who died in September 1973 as a result of complications from recreational drug use.[8] A review by Brooks and Wilson in The Spokesman-Review stated that album owed "little to fad or fashion", with compelling lyrics.[8] A review in the Toledo Blade again compared Crash Vegas to Cowboy Junkies, in which reviewer Doug Iverson stated the band to be "juiced up Cowboy Junkies" as it would "languish in quiet, elegant tunes"