[4] He performed for the first time as part of his guitar teacher's band (Tattoos 'N Whiskey), before progressing to play covers of Eric Church songs at local venues.

[5] In August 2022, Riegling won the Boots and Hearts Emerging Artist Showcase contest, securing him a single release with Universal Music Canada, songwriting sessions, and a trip to Nashville.

[6][7][8] In June 2023, Riegling signed a record deal with Universal Music Canada and released his debut radio single "Love (The Sweater Song)".

[11][12][13] In October 2023, he was an opening act for American country artist Tyler Hubbard on his solo headlining tour in Canada.

[1][14] Later that fall, Riegling joined Robyn Ottolini as the opening act for the Canadian dates on her "All My Friends Are Hot Tour".