Adam Gregory launched his career in country music when his first album, The Way I'm Made, was released in 2000 on Epic Records.

"[2] He met Billy Ray Cyrus while performing at Big Valley Jamboree in Camrose, Alberta.

Gregory went to Kabul, Afghanistan in 2003 for the OP ATHENA Show Tour from November 19 to December 5 to perform for the troops.

[7] Gregory also performed at West Edmonton Mall in 2005 to help raise money for the Canadian Red Cross to donate to the South Asia tsunami fund.

[10] Adam Gregory has continued to further develop his career in the entertainment industry through film, taking a leading role in the comedy Sharp as Marbles.

[11] Adam Gregory’s song “The World Could Use A Cowboy” was covered by Canadian Country Music Singer Ty Baynton in 2021 on his album Wrong Turns.

In October 2008, Cricket Communications partnered with Big Machine Records and Gregory for a promotional sponsorship with ringtones and in store events for the remainder of 2008.

[19] Although Big Machine went on to release Gregory's Crazy Days album in conjunction with Open Road Recordings in Canada, a U.S. release never happened, and Gregory left the label to focus on his songwriting and complete a series of tour commitments in his native Canada.