Best Country Singles of 2009, Part 1: #40-#21

Here’s hoping you haven’t gotten completely burned out on countdowns yet. 2009 was hardly a favorite musical year for many of us, but amid each year’s glut of throwaway items, there’s always a good’un or two (or forty). The following is the first installment of our Best Singles of 2009 list, which will conclude tomorrow morning. Best Albums will follow next week.

As with the Singles of the Decade feature, this countdown has been compiled through combination of four equally weighed Top 20 lists by Kevin, Leeann, Tara and myself. An inverted point system was applied to the individual rankings (#1 on a list meant 20 points, while #20 on the list meant 1 point). The songs were then ranked together by number of total points, greatest to least. The final result is another rather stylistically diverse set.

As always, we hope you enjoy the countdown, and welcome all the feedback you can muster. Happy New Year!


Lady Antebellum, “Need You Now”

The trio puts a country spin on an old school pop sound, but without forsaking raw emotion. The highlight of the song is Hillary Scott’s smoky performance, which draws out all the anguish and regret you’d expect from a desperate, 1 AM lover’s call. – Tara Seetharam


Joey + Rory, “Play the Song”

While Joey + Rory’s image appears to be squeaky-clean, it is fascinating that their songs have displayed some of the most attitude in the mainstream country music world. After releasing the sassy “Cheater, Cheater”, they have appealed to radio (the very people holding part of the duo’s career in their hands) to stop limiting their playlists with safe choices and to just “play the song.” – Leeann Ward


Toby Keith, “Cryin’ for Me (Wayman’s Song)”

A heartfelt tribute to a friend that has passed on, with a vocal that once again proves Keith to be among the finest the genre has ever seen. – Kevin Coyne


Rosanne Cash with Bruce Springsteen, “Sea of Heartbreak”

On her 2009 covers album, Rosanne Cash includes a rendtion of Don Gibson’s “Sea of Heartbreak.” She turns the song into her own with a jaunty production and the inclusion of revered rocker Bruce Springsteen, who channels a smoother sound than usual. – LW


Zac Brown Band, “Toes”

As tired as I am of picturing Zac Brown’s ass in the sand, his group delivered the best Jimmy Buffett send-up the genre has seen in many years of them. “Toes” is light and silly, to be sure, but light and silly can work when you paint them with detail and don’t over-amplify them. – Dan Milliken


Joey + Rory, “To Say Goodbye”

The matter-of-fact presentation somehow enhances the sadness by underplaying it. – KC


Charlie Robison, “Feelin’ Good”

Charlie Robison’s album Beautiful Day reflects his varied emotions after his divorce from Dixie Chick Emily Robison. While there is a lot of dark reflection on the album, there are sparks of hope for the future as well, though forced they may sometimes be. “Feelin’ Good” is one of those songs; it’s mixed with both optimism and leftover pain. – LW


Trace Adkins, “All I Ask for Anymore”

A humble confession of a man’s shifting priorities, sung with sturdy conviction and quiet confidence. It’s nothing groundbreaking for Adkins, but a home run nonetheless. – TS


Kellie Pickler, “Best Days of Your Life”

The chorus that will not quit helped make this the closest that Taylor Swift has ever gotten to heavy rotation in my world. – KC


Montgomery Gentry, “Long Line of Losers”

Yeah, I know. But I can’t help it. Every time my brain tells me to forget this sensationalized celebration of white-trash lineage, I listen to it again and the smile comes right back. There’s just something cool about being willing to accept the role your family has in shaping your identity, especially those parts of it that outsiders might look down on. – DM


Steve Azar, “Moo La Moo”

Good to know that the working man still has a voice being offered to country radio, even if they don’t choose to play him. – KC


Cherryholmes, “This Is My Son”

A mother’s prayers draw a sad parallel between her soldier son and her savior, as she realizes each has been sacrificed for “a people who don’t care that they’re free at the cost of his life.” It’s a wonder the group was able to make such a provocative message sound so pretty. – DM


Charlie Robison, “Reconsider”

Robison’s vulnerability is palpable in this song that wonders if he could somehow repair his failed relationship. While he asks “would you reconsider?”, it’s evident that he already knows the answer and it’s not good. – LW


Tim McGraw, “It’s a Business Doing Pleasure with You”

Funny as all get out, McGraw returned with an “I Like It, I Love It” for the new millenium. $48 and a thrown shoulder at the county fair would be getting off easy these days. – KC


Holly Williams, “Mama”

Songs that pay tribute to Mama are rather common in country music. Holly William’s version of the Mama tribute is different, however, as it looks through the lens of a daughter who is grateful to a mother for not trying to sabotage the daughter’s relationship with her father, even with plenty of valid ammunition to do so. The fact that we know that Holly Williams is the daughter of Hank Williams, Jr. only helps to add to the weight of the song. – LW


Brad Paisley, “American Saturday Night”

Paisley serves up his own brand of playful patriotism with this infectious ode to our melting-pot nation. It’s a splash of truth mixed with a heck of a lot of fun – a signature Paisley recipe. – TS


Zac Brown Band, “Whatever It Is”

There is no mainstream band who manages to sound more at ease than the Zac Brown Band. “Whatever It Is” magnifies the relaxed vibe that the group seems to naturally exude. Furthermore, the fact that they’re able to do it with a love song is refreshing in and of itself. – LW


Sugarland, “Joey”

Never-ending questions that will remain unanswered, fueled by guilt and helplessness that are unabated. – KC


Mark Chesnutt, “She Never Got Me Over You”

A slice of pure, timeless classic country, written by the late Keith Whitley and performed beautifully by one of our most talented traditional male vocalists. – TS


Emily West, “That Kind of Happy”

This is one of those rare instances when pop and country successfully collide to create a piece of irresistible ear candy. Emily West seems to be good at that. – LW


  1. Yes, I think a list of 40 is more appropriate for 2009 rather than 100 or 200. ;) Anyway, my favorites also include “Toes”, “Need You Now”, “American Saturday Night” and even “Long Line of Losers”. I couldn’t really get into “Cryin’ For Me” or “The Best Days of Your Life” though.

  2. I would have liked “Sea of Heartbreak” better without Springsteen. I can’t stand that guy and his voice just doesn’t mesh well with Rosanne’s.

    You can’t stand Springsteen? I’m sorry.

    I do actually prefer the contributions of Costello and Rufus Wainwright to Springsteen’s on The List, but I do really like “Sea,” too.

  3. Glad to see Sugarland, J+R, and Lady A. (That song [Need You Now] has quickly became my fav of theirs)

    I bet the last half will consist of Lambert’s “White Liar,” and i dont know what else…

    Suprised to see Pickler on the list, though.

  4. So I’m a bit surprised that Kellie’s song ranked higher than Lady A’s “Need You Now.” I think the Lady A song is more well written and better sung…but that’s just my opinion.

    By the way, I never get tired of countdowns! They’re so much fun to read and try to guess what will be number!

  5. I’m not a Springsteen fan, either, but his contribution to Rosanne’s “Sea of Heartbreak” doesn’t really bother me.

    To be honest, I really don’t like most of the songs on this list. That’s not a criticism of the CU staff, it’s just a reflection of the slim pickings you had to choose from. I do like “Sea of Heartbreak” and “That Kind of Happy”. I also like “All I Ask For Anymore” a lot and would have ranked it much higher.

  6. So I’m a bit surprised that Kellie’s song ranked higher than Lady A’s “Need You Now.” I think the Lady A song is more well written and better sung…but that’s just my opinion.

    I’m surprised that the Pickler song is on the list at all.

  7. To be honest, I really don’t like most of the songs on this list. That’s not a criticism of the CU staff, it’s just a reflection of the slim pickings you had to choose from.

    I enjoy most of the songs on the list to some extent, but it’s definitely a weaker group than we’re used to listing.

  8. So telling that we are all saying ‘slim pickings’. That seems to be the phrase of the era.

    Anyway, I do like this list – and agree with almost all of it so far. I particularly like the write-ups for the McGraw and Montgomery Gentry songs.

  9. I don’t like many of these songs either and where’s Jason Aldean, Darius Rucker, and Miranda Lambert? I’m not surprised to see a Kellie Pickler song since she’s one of the best singer-songwriters, Best Days of Your Life is a top 10 hit better than most singles, and country radio listeners rated it top 5. Country radio blocked it out of the top 5 because some stations don’t play Kellie’s songs people want to hear while they play other artists to death. Carrie, Taylor and Reba are the only women that have been allowed to chart #1 in about the past 5 years no matter how good Kellie, Miranda, and other women’s songs are. Best Days of Your Life is also a near platinum selling song. It should be on the #1-#20 CU list. It makes no sense that Taylor Swift’s You Belong With Me is #20, Fifteen is #6, Kellie’s Best Days of Your Life is #32, and Jason, Darius, and Miranda are missing. How did that happen? Are some CU staff huge Taylor fans? Best Days of Your Life is a great song, period. Kevin can’t get it out of his head because the melody is killer and like most of Kellie’s songs it’s very well-written and sung. Razor why are you surprised? Are you the X who got run over by a bus in the video? lol

  10. tc,

    I think I speak for a few people when I say that Miranda had some really good stuff out this year, but neither of her singles are the best representations of that. I enjoy “White Liar” as ear candy and am glad to see it give Miranda a big chart hit, but I don’t think the lyrics are up to her standard or make that much sense (is it really a “white lie” if someone pretends to not be cheating?). I did actually like Jason Aldean’s last two singles to some extent, but not enough to put them in my top 20. Darius Rucker’s material hasn’t lived up to his talents for me yet.

    The prominence of Swift on this list can be mostly attributed to me. I think Fearless is a great album, and they’ve picked exactly the right line-up of singles off it. I wouldn’t call myself a “huge fan,” but I have liked her a lot recently.

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