The Weekend Whiskey band was formed in Grafton, Ontario, in the late 1970s by Greg Eagleson (known as J.D. Eagle), Terry Davey, and Danny Burns. Initially a weekend project, the band's early experiences included working with iconic artists such as Stonewall Jackson and Canada's Honey West. Recognizing their passion for the music industry, Greg and Terry decided to relocate to Nashville to pursue a career in music.

Bobby Rich and Charley Gore, who played bass and steel guitar for Stonewall Jackson, played a crucial role in the band's early development by introducing them to key figures in the industry. Charley Gore facilitated a demo session with renowned studio guitarist Gerry Shook, which helped the band gain traction in the United States. Soon after, they were signed by Nashville manager Denny Ski, propelling them into the music scene.

By the early 1980s, Weekend Whiskey had performed at notable venues such as Fan Fair in Nashville, the famous Palomino in Hollywood, and Cajun’s Wharf in Nashville, owned by Lee Golden of the Oak Ridge Boys. During a west coast tour, the band opened for Garry Morris and Gus Harden in Los Angeles and followed Ricky Nelson at the Palomino, experiencing the fast-paced life of an emerging band.

At the Palomino show, manager Denny Ski arranged for the owners of Pike Records in Bakersfield to hear the band. Within two days, they secured a development deal and recorded tracks at Quad Tec studios, under the production of Bobby Burnett. However, the resulting album did not achieve significant success, leading the band to return to Canada to tour and refine their skills. Over the next four years, J.D. Eagle replaced and restructured the group, enlisting around 30 musicians, which contributed to the band's growing reputation.

During this period, they opened for artists such as Johnny Paycheck and Tanya Tucker, and made a cameo in the ABC movie of the week "American Harvest," featuring Wayne Rogers of MAS*H and Earl Holliman from Police Woman.

Seeking to enhance the band's dynamic, J.D. added Rob Sutherland, a well-known bassist from Western Canada, who had previously led his own band, Nechko, from Prince George, B.C. This partnership proved to be pivotal, as the two became dedicated collaborators both on and off stage. They eventually secured a spot on an emerging syndicated television show, where they shared the stage with the Desert Rose Band, featuring Chris Hillman of The Byrds. Although the show was never aired, the band continued to evolve by bringing in guitarist Doug Camire from Calgary and drummer James "Sparky" Westbury from Brandon, Manitoba. This lineup of four members has become synonymous with the Weekend Whiskey Band, although they often performed as a five-piece, incorporating various keyboardists such as Vince Schieveletto, Dewey, Dave Edwards, George Kinsmen, and Fred Kerr.

In the studio, Rob and Greg developed new material and chose to produce their album independently. "One Step Closer," recorded in Edmonton, achieved considerable success, notably with the title track and "Tonight," which garnered nominations for Video of the Year and secured top 10 status in five countries, albeit not in Canada.

By this time, the band had become one of the most sought-after live acts in North America, touring extensively from Las Vegas to Reno, California, Texas, and as far north as Dawson City in the Yukon. They opened for renowned acts such as Vince Gill, Little River Band, Lonestar, and Buffalo Springfield. Although a major breakthrough hit eluded them, Greg reflects on their journey without regrets.