Songfacts®:

• This was penned by Nashville songwriter Don Simpson (Brad Paisley's "Waitin' on a Woman," Garth Brooks' "Mom") and originally recorded by The Charlie Daniels Band for their 1989 album Simple Man.
• Chris Stapleton explained why he recorded the song for his Traveller album: "When I first moved to town I got invited by Steve Leslie, who brought me to town, to a songwriter round. I'll never forget it. It was Steve, Wynn Varble, Kevin Denny and Don Sampson. They took turns playing songs they had written. They went through a few rounds and when it got around to Don Sampson's turn he told the story that he had written this song on a Pizza Hut napkin and that every word was true. That song was 'Was It 26' and at the time I think it was the only song Charlie Daniels had recorded that he hadn't written. That was the moment I realized the importance of the songwriter.
  
  Even though I was barely 23, 'Was it 26' was a song that I had in heavy listening rotation. Don and I wound up writing at the same publishing company for a number of years. I told him not long after that first time I heard him play it how much I loved that song and he said, 'Maybe someday when you're older you can record it.' And now I have."