My Kind of Country

Country music from a fan's point of view since 2008

Decade in Review: Occasional Hope’s Top 50 Singles

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.

39. Takin’ Off This Pain – Ashton Shepherd
For a while in 2008, Ashton was being touted as the salvation of country music. I was slightly dubious about that, and this, her debut single just failed to hit the top 20, but I do really like it, and Ashton has one of the most distinctive voices in modern country music.

38.  Sounds So Good – Ashton Shepherd
She followed that up with the charming and atmospheric feel-good song about the sounds of rural life in the summer.

37. It’s A Great Day To Be Alive – Travis Tritt
Travis’s supremely relaxed version of Darrell Scott’s song reached #2 in 2001.

36. Wrapped Around – Brad Paisley
This charmingly effervescent love song from Brad was another #2 hit in 2001.

35. Don’t Ask Me How I Know – Bobby Pinson
Gravel-voiced Bobby Pinson has made a career as a songwriter, but he started out as an artist in his own right. This was his only hit, a top 20 in 2005 with a nicely wry lyric recounting various life disasters, by turns funny and serious.

34. Songs About Rain – Gary Allan
I’ve always loved songs which refer to other songs, and this one does just that, using songs about rain on the radio to underline the protagonist’s mood as he deals with a loved one leaving. It reached #12 in 2003.

33. Startin’ With Me – Jake Owen
This candidly regretful confession of past mistakes was a #6 hit for Jake in 2006, and is by far the best thing he has ever recorded.

32. I Am A Man Of Constant Sorrow – The Soggy Bottom Boys
The oldest song on my list is a traditional folk/oldtime/bluegrass number which achieved new fame by its inclusion on the soundtrack of the movie O Brother Where Art Thou, the success of which sparked something of a revival in acoustic music. Lead vocals on this version, which senaked into the top 40 and won the CMA Single of the Year Award, were taken by Alison Krauss band member Dan Tyminski.

31. Gunpowder And Lead – Miranda Lambert
Miranda is probably the biggest star so far to get her start on Nashville Star, finishing third in the first season. My favorite Miranda Lambert single, and her biggest hit to date, is this hypnotically insistent rocker about an abused woman planning on shooting her partner on his release from jail, which rached #7 in 2008.

30.Drinkin’ Me Lonely – Chris Young
My favorite Nashville Star winner Chris Young performed this on the original songs week of his season of the show, and it almost certainly helped him to win. It was accordingly released as his debut single in 2006. A sad, traditional sounding lament, this deserved to do much better on the charts than #42, and Chris had to wait until 2009 to make a chart breakthrough (with inferior material).

29. Celebrity – Brad Paisley
Brad took a swipe at reality shows in one of the best of his comic songs. This trenchant satirical take on the reality TV route to fame and the desire to be famous for nothing in particular was a #3 hit in 2003, before the Idol effect had really hit country music. It probably couldn’t be a hit today.

28. My Name – George Canyon
This emotional 2005 single from Canadian Nashville Star contestant George Canyon’s only US album, One Good Friend, has a very unusual protagonist – it voices the dreams of an unborn child who eventually is miscarried. Canyon’s sweet tenor works beautifully. It won’t be to everyone’s tastes, but I find it deeply moving.

27. I Love You This Much – Jimmy Wayne
This is another song some will find too sentimental, but which I find deeply moving. Jimmy’s more recent music has been too pop for me, but his first album contained a number of contemporary but effective emotional songs inspired by his tough background, including this tale of a difficult paternal relationship which was a top 10 hit in 2003. It opens arrestingly with the admission that a child’s father probably doesn’t love him, and builds from there, with a religious payoff.

26. How Do You Get That Lonely? – Blaine Larsen
This sensitive look at teenage loneliness and suicide was a top 20 hit for teenager Blaine Larsen in 2005. It was written by Rory Lee Feek (who discovered Blaine) and Jamie Teachenor. I like it because the emotional heart of the song rests not in the fact that the boy who kill himself was so depressed as to take his own life, but on the point that no-one actually realized how he was feeling beforehand.

25. Whiskey Lullaby – Brad Paisley featuring Alison Krauss
The deeply depressing story, written by Bill Anderson and Jon Randall, recounts a man drinking himself to death, followed by his wife, but the mood is lifted by Alison Krauss’s enchanting harmonies. This beautiful record reached #3 in 2004.

24. Give It Away – George Strait
Bill Anderson also co-wrote my favorite Strait single of the decade, together with Buddy Cannon and Jamey Johnson. The part-spoken tale of the end of a relationship weas a #1 hit in 2006.

23. Nothing On But The Radio – Gary Allan
This sexy #1 was a hit for Gary in 2004.

22. She’s Pretty – Star de Azlan
Star raised my hopes by releasing this wistful, traditionally-oriented single in 2008, but is the only artist on this list never to have released a full album. As she is signed to Curb, I can possibly look forward to something sometime in the next decade.

21. If Heaven – Andy Griggs
This is my personal equivalent of a one-hit wonder. Andy Griggs’ previous hits all seemed pretty bland and uninteresting to me, but this one single, which reached #5 in 2005, was perfect. The main credit should go to songwriter Gretchen Peters, whose carefully constructed lyric incorporates sad and hopeful emotions in just the right way, but Andy’s phrasing is just right too.

20. Ol’ Red – Blake Shelton
I first heard this song when George Jones recorded it in 1990, and I loved it then. Blake is no George Jones, but he’s a good singer and this funny and atmospheric story song would be entertaining no matter who did it. It was a top 20 hit in 2002.

19. Cheater, Cheater – Joey + Rory
Another act emerging from a reality show, the husband=-and-wife team finished third in Can You Duet in 2008. This song, an irresistible slice of fun, really stole the whole season. Subsequently relased as their debut single, the outraged wife’s diatribe was a minor hit. The use of the word “ho” may have been a step too far for country radio.

18. Heartbreak Town – Dixie Chicks
In contrast, this song written by Darrell Scott about failing to achieve dreams of stardom was probably just a little too bleak to reach the top 20 hit in 2001.

17. I Just Came Back From A War – Darryl Worley
The decade was dominated in many respects by war in Afganistan and Iraq. There were a number of gung-ho singles on the subject, but none was as convincing to me as this disenchanted look at a bewildered soldier’s return home. It was a top 20 hit in 2006.

16. Easy Lovin’ You – Chalee Tennison
Chalee was an artist who I always thought should have made it, but for some reason radio didn’t appreciate her throaty alto and excellent songs. This non-charting single from Chalee’s 2003 Dreamworks album Parading In The Rain is a one-time teenage single mother’s tender tribute to her child.

15. Last Call – Lee Ann Womack
After a detour to a more pop sound earlier in the decade, Lee Ann reverted to real country with her very retro 2005 album There’s More Where That Came From, but the relative commercial failure of that meant that her follow up, 2007’s Call Me Crazy was a slightly uneasy mix of traditional and pop country. The lead off single (which peaked at #14 in 2008) was a true highlight, though, and one of LeeAnn’s finest recordings, with a beautifully judged vocal performance which perfectly conveys the lyric with its resigned look at a relationship on its last legs.

14. Three Wooden Crosses – Randy Travis
Randy Travis spearheaded the commercial impact of the new traditionalists in the late 80s, but has spent much of this decade recording religious material. Even his secular singles have been ignored by radio, but somehow this emotion-laden story song with a neat twist (written by Kim Williams and Doug Johnson) managed to make it all the way to #1 in 2003, and it was named the CMA Song of the Year.

13. Cheapest Motel – Tracy Byrd
Tracy’s chart streak ran out in the middle of the decade, but he released perhaps the best work of his career afterwards. This tart morality tale of a man whose cheating leads to losing everything he didn’t realize he valued in his life may have been too traditional for country radio in 2006, or maybe it was just the problem of being on an independent label. You can find it on his excellent 2007 album Different Things.

12. Travelin’ Soldier – Dixie Chicks
This was the song at #1 when the Chicks fell from grace with country radio in 2003. In its own right, it’s a fine story song written by Bruce Robison about a young soldier killed in Vietnam and the even younger girl who loves him. It had previously been recorded by Ty England, but this version is the definitive one.

11. In Color – Jamey Johnson
Jamey Johnson’s top 10 from 2008 deservedly won this year’s CMA Song of the Year. A beautifully constructed song about the difference between memory and hearing about life events second hand, it bears witness to the Depression and World War II, as well as to its subject’s emotional life.

10. Without You – Dixie Chicks
This #1 from 2000 is a bleak ballad about the desolate end of a relationship, written by Natalie Maines with Eric Silver, and represents the Chicks at their best musically.

9. If You Can – Tammy Cochran
Tammy’s big hit was the autobiographical and sentimental ‘Angels In Waiting’. I like that, but prefer this superb ballad with its perfectly measured vocal, addressed to a cheating husband, and challenging him to walk away from their marriage “if you can”. It was Tammy’s debut single, and just missed the top 40 in 2000, although she and the label felt strongly enough about the track to include it on both her first two albums.

8. Murder On Music Row – George Strait and Alan Jackson
Technically this was not officially released as a single, but despite its criticism of the industry, it got enough radio airplay in 2000 to sneak into the top 40, after being debuted on the CMA Awards show in 1999. The biting metaphor addressed the state of country music in the late 90s, when pop and rock influences were starting to dominate. A decade on, things have only got worse, and the song (written by bluegrass songwriters and musicians Larry Cordle and Larry Shell) seems more topical than ever.

7. One Second Chance – Jeff Bates
Jeff’s most successful chart singles were sexy love songs, but I think his finest recording was this single from his independent second album, which barely charted in 2006. It is a deeply emotional story song about a guy who has made a serious mistake and spent time in prison, and can’t get a break from potential employers or the mother of his child.

6. The Upside Of Being Down – Catherine Britt
When I first heard this 2004 single from young Australian Catherine Britt, a charming and slightly tongue-in-cheek look at the bright side of being dumped by a boyfriend, I was convinced she was going to be a huge star. Sadly it didn’t work out that way, and the excellent album she recorded for RCA was not formally released in the USA at all.

5. Wake Up Older – Julie Roberts
Mercury artist Julie was another great singer who never really made a breakthrough on the charts, although at leasst she got to release two albums. Her most successful single was the top 20 ‘Break Down Here’, but I think this expression of despair over a relationship which has ended (written by Lisa Carver) is superior, although it faltered before getting to the top 40 in 2005.

4. Monday Morning Church – Alan Jackson
The desolate sadness of the lyric and Alan’s delicately measured performance, together with Patty Loveless’ harmony vocals, make this tale of lost faith following bereavement a genuine masterpiece, although it only reached #5 in 2004. This beautiful song was written by Brent Baxter and Erin Enderlin.

3. Stay – Sugarland
The best contemporary country song of the decade was this cheating song from 2007. Surprisingly, it only reached #2, although it won Grammy, CMA and ACM awards.

2. High Cost Of Living – Jamey Johnson
My #2 spot is taken by a single from earlier this year which was so controversial that even following up ‘In Color’ it couldn’t crack the top 30. It remains an excellent dark morality tale, as Jamey’s brooding vocal remorselessly recounts the protagonist’s failings and fall from grace. Not exactly autobiographical, but clearly inspired on a subconscious level by aspects of Johnson’s life, this intense song is a modern masterpiece, and one of the very few singles from the last year that is worth hearing.

1. Where Were You (When The World Stopped Turning?) – Alan Jackson
This was the most obvious choice in my entire list. Not only was it a great song, but it truly captured the mood of a nation, if not virtually the entire world, in a way very few songs can do. Alan first performed this song live on the CMA Award show in November 2001, and I understand that initially he had no intention of recording it at all, least of all making it a single. But the public response was so overwhelming that there was no question that it had to be a single. And it duly went to #1 early in 2002.

11 responses to “Decade in Review: Occasional Hope’s Top 50 Singles

  1. Razor X December 29, 2009 at 9:12 am

    Excellent list; not much to take issue with here. I agree that “Does My Ring Burn Your Finger” was the best song on I Hope You Dance . It’s one of my favorite Lee Ann Womack singles ever.

  2. Lep December 29, 2009 at 11:03 am

    Wow, your tastes greatly overlap with mine. Props for including “One Second Chance” and “I Just Came Back from a War”, two of the most criminally overlooked singles in recent memory. I’m glad I’m not the only one who thinks “Startin’ with Me” is a great song. Shame Jake Owen hasn’t released anything worthwhile since. There’s still about five of these songs I haven’t heard yet. Excellent list.

  3. Michael December 29, 2009 at 11:20 am

    Great list. I agree with you on the Toby Keith videos. It’s nice to see the Jake Owen and Blaine Larsen songs, a couple of Gary Allan hits, cuts from the Dixie Chicks, “High Cost of Living”, “Monday Morning Church” and “Does My Ring Burn Your Finger.” I would have probably selected different Paisley and Strait tunes, however. Maybe “Welcome To the Future”, “Letter To Me” or “When I Get Where I’m Going” over “Wrapped Around” and “Celebrity” and “You’ll Be There” or “Desperately” over “Give It Away”. Also, I actually enjoyed a couple of the songs from Andy Griggs’ debut album and “Break Down Here” over “Wake Up Older”. Thanks again. A very enjoyable read! Happy New Year! 🙂

  4. Pingback: Sarah Buxton’s Debut Gets Release Date; ‘Country Weekly’ Creates Archive of Covers | The 9513

  5. Bob December 29, 2009 at 1:20 pm

    Good list. I like the songs you included by less successful artists such as George Canyon, Andy Griggs, Blaine Larsen and Catherine Britt. (Another outstanding Aussie who didn’t make it here is Melinda Schneider who I saw at the Bluebird 2 1/2 years ago.) I’ll have to check out the Tammy song which I’ve never heard. For Julie Roberts, I prefer songs that were not singles from her debut cd – “You Ain’t Down Home”, “Unlove Me” and “Rain on a Tin Roof”.

    Of the more established artists, I’m glad to see Diamond Rio’s “One More Day”, Jo Dee Messina’s “I wish” and the Josh-Trisha duet. “I Still Miss Someone” was covered by Suzy Bogguss on her 1994 cd “Simpatico”. For Jimmy Wayne, I would have chosen “Stay Gone” but I liked his debut cd.

    AJ just may be a better song writer than he is a singer. “Where Were You”, “Remember When” and “Drive” were some of his solo writing efforts plus he co-wrote many others. He has 127 writing credits on ASCAP.

  6. Leeann Ward December 29, 2009 at 5:17 pm

    The Bogguss version with Vince Gill is my favorite of “I Still Miss Someone.” Great production, not to mention the singers.:)

    Interesting list. I don’t agree with all of it, but it’s thoughtful.

  7. Derrick December 30, 2009 at 12:47 am

    Tough to argue, once again. Making a list like this is going to leave lots of room for disagreement, and mostly I would change the order around. The biggest thing I want to mention is how happy I am to see “Wake Up Older” — can’t imagine how many times I listened to that song and lamented why Julie Roberts didn’t strike it big.

    “Last Call” is such a classic old school country tune. Great to see it here. For fun, “Pour Me” by Trick Pony might squeeze in, since it came out in 2000 IIRC.

  8. SamB December 30, 2009 at 7:18 am

    Wow, great to see a Catherien Britt song on an end of decade list! Great song, though personally I prefer Too Far Gone

  9. Pingback: Best Of The Decade Lists « Nicholasjensen's Blog

  10. Dave Whitaker February 5, 2010 at 6:14 am

    As an aficionado of lists about all things music, I have developed a website ( and now a Facebook page (!/pages/Daves-Music-Database/300371661944?ref=mf). In an interest in building a community around such interests, you are invited to join the latter. Recently, links to more than 60 best-songs-of-the-decade list have been added, including yours. Come on over and check out what others have picked as the decade’s best songs.

    Dave Whitaker,

  11. DiDi Mishnau February 1, 2011 at 8:19 pm

    Great list, nice to see “I Wish”, “If Heaven”, and “Whiskey Lullaby”–some of my favorites. Also, the very patriotic songs, some of the very best!

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