[2] While in school, Cockrell discovered his love of country music and rock n' roll, which was forbidden in his home.

AllMusic gives a favorable review of Cockrell's debut, describing his voice as "the kind of high, lonesome warble that can raise the hair on your neck and put a tear in your eye", and the album as "striking a nice balance between not-so-rowdy honky tonk and heart-worn balladry".

[5] Allmusic proclaimed that the album is "pure country music, untainted by commercial considerations and without rock influences".

[7] Alternative country magazine No Depression praises Cockrell's lyrics as "straightforward simplicity", and also compliments the singing on the album as "intimate, immediate and intentionally under-rehearsed to capture an edge of freshness".

[3] After the three Yep Roc releases Cockrell moved to Nashville to focus on songwriting for financial reasons.

[2] However, reflecting a desire to "write less and find a community where he could be more than a musician", Cockrell left Nashville to return to North Carolina.

[2] During his time in Nashville, Cockrell co-wrote and recorded a duet with Mindy Smith for her 2007 Christmas album My Holiday, entitled "I Know the Reason".

[10] In the spring of 2016, Cockrell announced that he was working on his fifth solo album If In Case You Feel The Same, which was released via ATO Records in 2020.

The host and comedian Jimmy Fallon heard Cockrell's song "Swingin'" at a hardware store during the COVID-19 pandemic, and used Shazam to find the track, and was so drawn to it that he wanted Thad to perform on the show.