Inevitably, anyone’s list of their favorite singles of the decade is going to be more mainstream-oriented than one of the best albums over the same period, just because independent artists are less likely to get their singles played on radio, and they tend to release fewer. My list doesn’t consist solely of hits, but a good proportion did get the success they deserved.
50. I Still Miss Someone - Martina McBride featuring Dolly Parton.
Martina recruited Dolly Parton to sing harmonies on her cover of this Johnny Cash classic on her Timeless album in 2006. It didn’t appeal to country radio, but it is a lovely recording.
49. How Do You Like Me Now?! - Toby Keith
The only song where Toby Keith managed to exercise his giant ego yet seem appealing at the same time. This #1 hit from 2000 is meanspirited but somehow irresistible. The video’s a bit heavy-handed, though.
48. I Hope You Dance - Lee Ann Womack
The enormous crossover success of Lee Ann’s signature song in 2000 set her on the wrong path musically for a while, but that doesn’t detract from the song itself, a lovely touching offering to LeeAnn’s daughter, featuring additional vocals from the Sons of the Desert.
47. You Shouldn’t Kiss Me Like This - Toby Keith
Toby is a very hit-and-miss artist for me, but he makes his second apearance in this list with my favorite of his singles, the tender realization on the dancefloor that a friend might be turning into a romantic interest. It was another #1 hit, this time in 2001. It has another terribly conceived video, though.
46. The Truth About Men - Tracy Byrd
Tracy Byrd recruited Blake Shelton, Andy Griggs and Montgomery Gentry to sing on this comic song about gender differences. Of course it’s not universally true – but it’s quite true enough to be funny. The single was a #13 hit in 2003, and is one of the few singles of recent years to inspire an answer song – Terri Clark’s ‘Girls Lie Too’, which was an even bigger hit the following year but has worn less well.
45. I Wish - Jo Dee Messina
Jo Dee Messina’s glossy pop-country was very accomplished but not always to my taste. But I did love this relatively subdued ballad which appeared only on her Greatest Hits album in 2003, and reached #15 on Billboard, with its neat twist as the protagonist bravely wishes her ex best, before admitting, “I wish you still loved me”.
44. Does My Ring Burn Your Finger - Lee Ann Womack
This biting reproach to a cheating spouse, written by Buddy and Julie Miller, was the best moment on Lee Ann’s bigselling I Hope You Dance. It was the least successful single from it, however, only reaching #23 in 2001.
43. Long Black Train – Josh Turner
Josh is one of the few traditionally oriented artists currently on a major label, although he has often recorded material which is not quite worthy of his resonant deep voice. His debut single was a heavily allusive religious song about sin which, although it only got to #13 in 2003, really established him as a star.
42. One More Day – Diamond Rio
A #1 hit from 2001 about bereavement and longing for more time with the loved one who has been lost, this touching song has heartfelt vocals and lovely harmonies from one of the best groups in country music over the past 20 years.
41. Another Try – Josh Turner and Trisha Yearwood
A classy ballad about hoping for better luck in love from two of the best mainstream singers around, this reached #15 in 2008, but should have been a #1.
40. I Still Sing This Way – Daryle Singletary
In 2002 Daryle had a single out called ‘That’s Why I Sing This Way’ (written by Max D Barnes) declaring himself a real country singer (“Mama whupped me with a George Jones record, that’s why I sing this way”). Five years later Daryle himself co-wrote this sequel, which I like even more, as he looks wryly at the music industry’s demands for glitz and glamor. He tells his manager he’s fine with a change of image – but he can’t change the way he sings.
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