[6] According to Asleep at the Wheel frontman Ray Benson, the title Half a Hundred Years was conceived during a conversation he had with singer-songwriter Jamey Johnson at an Austin City Limits performance in 2020.

[9] Benson and fiddler/vocalist Katie Shore initially began recording tracks for the album at the frontman's home studio, with the rest of the current band members coming in later to add their parts.

Later, former band members also contributed to a range of songs, with a lineup of Benson, bassist Tony Garnier, pianist Floyd Domino and drummer David Sanger recording basic tracks for the host of guest performers to overdub their parts later.

Reviewing the album for online country music magazine Holler, Hal Horowitz wrote that "The 19-track, hour playing time zips along with so much enthusiasm that it feels half as long.

"[10] Similarly, Gary Whitehouse of the website A Green Man Review praised several elements of the album, including "Word to the Wise" featuring Bill Kirchen, "the big band tracks that really get my feet tapping and heart beating", and the instrumental "The Wheel Boogie".