Wills has released five albums – Man with No Past (2010), If It Was That Easy (2012), Crazy Enough (2014), Tougher Than Love (2016) and an EP Longshot Bar & Grill (2019).
Many of his singles have made it onto the Billboard Canada Country Chart, including the hits "Somebody Will", "Down by the River", and "Won't You Be Mine", which each peaked at the number 9 spots.
[3] At an open mic night, Wills' friend bet him $20 that he wouldn't go on stage and sing a song with the band.
[7] Wills accepted the bet, sang "The Dance" by Garth Brooks, and received an overwhelmingly positive reaction from the crowd.
[8] When Wills returned home from his travels, he discovered that his biological mother had also registered with the adoption agency, and that she was requesting contact with him.
[7] He recorded demos in Toronto with Thomas Wade,[9] and then began to split his time between Calgary and Nashville to commit to making country music.
[10] While in Nashville, Wills began working with producers Mike Pyle and Walt Aldrige, who helped him develop his craft.
[2] In 2014, Wills released his third album, Crazy Enough, which was recorded entirely at the Music Centre Canada studio in his hometown of Calgary.
[13][12] Wills cites Garth Brooks, George Strait, Keith Whitley, Waylon Jennings, Lefty Frizzel, and Merle Haggard among his musical influences.