[1][2] He is best known as the singer for the rock band Legendary Shack Shakers, and is also an accomplished harmonica player, having recorded for such artists as Merle Haggard, Sturgill Simpson, John Carter Cash, Mike Patton, and Hank Williams III in the American Masters film "Hank Williams: Honky Tonk Blues".

[4] Wilkes is known as the founder and only remaining original member of the Legendary Shack Shakers, a rockabilly and blues band he formed in Murray, Kentucky, in the mid-1990s.

[10] In 2006, Wilkes, began work on a documentary film titled Seven Signs, that explored "music, myth, and the American South".

[12] In early 2009, Wilkes formed The Dirt Daubers, an old-time roots-influenced side project with his now ex-wife, Jessica, and "Slow" Layne Hendrickson.

He also reprised his "gothic preacher" character (developed for Shooter Jennings' The Real Me video) when he acted as the presenter at the 2013 Addy Awards in Cincinnati, Ohio.

Wilkes was met by author/actor/playwright and deputy Lord Mayor Gerard Mannix Flynn at the Mansion House in Dublin, where the two exchanged gifts as part of a UNESCO-sponsored reception.