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!

#40

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

#39

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

#38

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

#37

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

#36

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

#35

Joey + Rory, “To Say Goodbye”

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

#34

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

#33

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

#32

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

#31

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

#30

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

#29

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

#28

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

#27

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

#26

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

#25

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

#24

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

#23

Sugarland, “Joey”

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

#22

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

#21

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