The label has released more than 40 audio and video recordings by singer-songwriters Prine, Kris Kristofferson, Daniel "Slick" Ballinger, Shawn Camp, Dan Reeder, and Todd Snider, along with a dozen reissues of classic country music artists.

[5] The new Oh Boy label's first release was a red vinyl Christmas single with Prine singing "I Saw Mommy Kissing Santa Claus" on the A-side and "Silver Bells" on the B-side.

In 2007, Oh Boy released Standard Songs for Average People, an album of classic country duets by Prine and bluegrass singer Mac Wiseman.

Guest artists on the album include Brandi Carlile, Jason Isbell, Amanda Shires, and Dan Auerbach.

Burt was introduced to the label by Jody Whelan, who had discovered the folk singer's album Caught It from the Rye.

[13] In June 2020, Oh Boy Records signed Ohio-based country singer Arlo McKinley, marking him as the last signee by John Prine.