[6] It was during his time with Dirt Ball and Mudd Helmet that Freed designed show posters, adopting an "outsider" style that would influence his later works.
[2] Freed became acquainted with the Drive-By Truckers (DBT) in 1997, when they were invited to play in the first Capital City Barndance, a show designed to reflect the long lived Old Dominion Barn Dance with the addition of folk and rock artists as well as traditional country.
As DBT grew in fame and sales so did Wes' art which adorned backdrops, drum kits and roadie boxes up until his first album cover for the band Southern Rock Opera.
[7] He continued to design posters,[5] T-shirts,[10] backgrounds, and miscellaneous merchandise for DBT,[5] as well as the artwork in the 2009 documentary about the Truckers, titled The Secret To A Happy Ending.
He released in 2019 The Art of Wes Freed – Paints, Posters, Pin-ups and Possums,[12] a coffee table book that compiled his most notable works.