This was written by Ronnie Dunn and his frequent collaborator Terry McBride.
Dunn explained this tale of a father who teaches his daughter to hold her head strong through the tough times to CMT News: "The cowgirl thing is a theme they learn early on - to tough it out. It applies to horses so much with the principles you have to learn and the discipline you have to learn to keep the horses up. You fall off the horse, you get up. You don't cry, or you cry a few times at first, and you get over it. They're tough girls, but they're sensitive, too. They're women at the same time. They learn through the process to curb those emotions. It's good to draw them out if you can. That's what the last verse of 'Cowgirls Don't Cry' is about: You're going to cry whether you want to or not."
An alternate version of this song, which features Reba McEntire's vocals became a hit after she and the duo performed the song on the 2008 Country Music Association Awards. When this entered the Top Ten of the Billboard country charts, it became McEntire's 56th Top Ten Country hit, overtaking Dolly Parton's record for the most Top Ten Country hits for a solo female.
Dunn admitted to Great American Country that the idea for the duet with McEntire was sparked from a little friendly competition. He explained: "She e-mailed me back about every other week going, 'Are you gonna cut that song? 'Cause if not, I am!' So we finally called a truce, and we're doing it together."
Dunn told Great American Country that he first came across the phrase 'Cowgirls Don't Cry' on a T-shirt. He explained: "I saw it - the title - on a T-shirt at the Iowa State Fair. Terry McBride and I were on the bus, and I started talking about it... and we started talking about Reba and hearing her talk about how she grew up, how rough she thought her dad was on her in her rodeo days. We wrote it and sent the lyrics to her that night."