Although it's not something I like saying - now that we have a big buzz around the excellent "new level" Blown Away album, I'll be honest and admit that I found "Play On" the most disappointing of Carrie's four major release albums. (Paradoxically, though, it did contain one song that I regard as among the very best that Carrie's recorded - but more of that in later rounds!)
These two songs, though, for me illustrate what I did find disappointing about the album as a whole - namely, that, while good as a "holding exercise", they did little to enhance Carrie's reputation for depth as an artist. "Cowboy Casanova" was a big success for Carrie, and a favourite for many fans, but I'm afraid it didn't do a lot for me. While it shows a feisty attitude, I didn't find either the lyrics or the music held much interest - the contrast with the musically varied and vocally challenging "Good Girl" puts the later song in an entirely different league and illustrates for me the big leap in standard to the fourth album.
In this round, therefore, I'm going for "Mama's Song". It's been suggested earlier that saying "it meant a lot to Carrie" would be a cop-out "sympathy" vote - but I don't agree. The fact that it did mean a lot to Carrie meant that she gave it a pure and believable vocal, which compensates for its admittedly rather limited lyrical line. The music, too, is a good match for the mood of the theme. So while I'm not saying that MS was among the greats of Carrie's musical career, I do find it a sincere and disarming example of her slower songs - and one that made a bigger impact on me than CC.