[1] He has also released nine singles, achieving 5 number one Canada Country hits with "Lucky", "All Night to Figure It Out", "More Drinkin' Than Fishin'", "She Don't Know" and "Telluride".
He tended crops and raised livestock with his father before initially heading to Alberta for work at age 19.
[2][3] Eagleson cites Paul Brandt as one of his biggest musical influences,[4] while also viewing Alan Jackson, Randy Travis, George Strait, and Shania Twain as major idols.
[18][19] In April 2020, Eagleson released his fourth single "Close",[20] which would peak at #8 on the Canada Country chart, and #88 on the Canadian Hot 100 (a new career high).
[9] Shortly after, he released the single "More Drinkin' Than Fishin'", a collaboration with fellow Canadian country artist Dean Brody.
[24][25][26] On November 12, 2021, Eagleson released his second studio album, Honkytonk Revival,[27] which included "All Night to Figure It Out" and "More Drinkin' Than Fishin'" as well as the single "She Don't Know".
In the summer of 2024, Eagleson supported Cody Johnson as an opening act on the Canadian dates of his "The Leather Tour".
[39] In July 2024, he released a new version of the song "Do It Anyway" featuring American country artist Jake Worthington.