Jon Lanford, known as a touring musician, welsch by birth, transplanted to Chicago long enough ago to be a local now. Langford donated the amazing art work on the poster, inspired by a photo of Prine in the bathroom, adding the “cigarette 9 miles long” that Prine smokes in the aptly titled tune, “When I get to heaven.”

Langford has painted portraits of famous and forgotten figures from the dawn of country music, such as Hank Williams, Johnny Cash, Elvis Presley, and "The Cuckoo", many based on classic photographs. Many of his paintings and prints are available from the Yard Dog Art Gallery in Austin, TX, and LeMieux Galleries in New Orleans, LA, and Hatch Show Print Gallery in Nashville, TN as of 2021. Nashville Radio, a collection of his artwork and writings, was published in 2006.

Langford has designed and painted the covers for many music recordings. These include, but are not limited to, most of the recordings on which he has been the musical leader, and many recordings of his other bands. Other examples include the cover art of The Sandinista! Project – A Tribute to The Clash and "Commercial Suicide Man" (2018), collaborative single by the Nightingales and Vic Godard.

In 2015, Langford was commissioned by the Country Music Hall of Fame and Museum to paint a series of portraits for its "Dylan, Cash, and the Nashville Cats: A New Music City" exhibition, which opened on 27 March 2015. Of that exhibit, per Langford, "I said to my wife, 'They’ve got ‘The Death of Country Music’ on the wall at the Country Music Hall of Fame', and she just went, 'Well, I guess you won, then.'.” That commission lead to a collaboration between Langford and Hatch Show Print Master Printer Jim Sherraden. Their artwork was then adapted for the album covers of the 2015 double-LP compilation Dylan, Cash, and the Nashville Cats: A New Music City and of the 2016 triple-LP Trio: Farther Along by Dolly Parton, Linda Ronstadt, and Emmylou Harris.

Langford has designed the graphics for T-shirts, tote bags, and other items to support various organisations, including: Chicago's StreetWise magazine (which is sold by people who are homeless or at risk of being homeless); Chicago's Hideout Inn during the COVID-19 pandemic; Chicago's Old Town School of Folk Music; and San Francisco's Hardly Strictly Bluegrass festival. Langford's paintings appear on bottles and other items for the Dogfish Head Brewery, and Few Spirits. Since 2015, Langford has designed covers for a series of novels by author Jay Spencer Green, including Breakfast at Cannibal Joe's and Ivy Feckett is Looking for Love.

For over 10 years, Langford illustrated the pop-music parody comic strip Great Pop Things under the pseudonym Chuck Death with a friend from his hometown, Newport, Wales, Colin B. Morton, who wrote the text. The cartoon strip was published in music and alternative weekly newspapers in London, Los Angeles, and Chicago, and was a pen-and-ink history of rock-and-roll. An anthology of the best strips was published in a book of the same name.