My Top 50 Country Singles of 2000-2009
10 years ago, I listed my favorite singles of the 2000s, and did posts writing about my favorite rock, pop, R&B and rap songs of the decade. Last year, when I did the same for the 2010s, I covered the same genres and added country to the lineup. I'd like to go back and do lists for the '90s and other decades, and I feel like it'd be weird if I did country lists for every decade except the 2000s, so I'm just filling in that gap here. I really do love a lot of these songs and had fun revisiting them, though, they take me back to a time when watching CMT or putting on a country station was kind of a fun novelty for me as I got better at exposing myself to a genre that I like but didn't really grow up on. Here's the Spotify playlist of 49 of these songs (Garth's stuff is only streaming on Amazon).
1. Sara Evans - "Suds In The Bucket" (2004)
#1 Hot Country Songs, #33 Hot 100
Sara Evans recorded plenty of nice, slick pop country, including a cover of Edwin McCain's power ballad "I Could Not Ask For More," but her biggest hit was also her most country, the surprise smash third single from her fourth album. It's a simple little love story told as small town gossip, cute and full of characters like the outraged preacher and the biddies in the beauty shop, but the song is ultimately swept up in the emotion of teenage love, not the judging eyes of the townsfolk.
2. Keith Urban - "Somebody Like You" (2002)
#1 Hot Country Songs, #23 Hot 100
Keith Urban's stuff rarely scans as country to me, a lot of it just sounds like the king of big shiny guitar-driven pop/rock that started leaving the rock charts in the '90s and took safe haven on country radio. But he's great at it, so it's hard to argue with songs as catchy as "Somebody Like You," which does have a pretty great little prominent banjo part, and is even better with the extended jammy outro on the album version. It was produced by Dann Huff, a guy who's been kicking around the music industry so long that he played guitar on Whitesnake's "Here I Go Again" and Madonna's Like A Prayer, before becoming one of Nashville's most reliable hitmakers of the 21st century.
3. Taylor Swift - "You Belong With Me" (2009)
#1 Hot Country Songs, #2 Hot 100
Taylor Swift's best early country hits kind of sounded like power pop with a little banjo deep in the mix too, so I'm not too surprised that she abandoned country entirely on her way to become one of the biggest artists of the 21st century. But "You Belong To Me" is still her high watermark for me, I don't know if she's really touched it in all those dozens of subsequent hits. I like the lyrics about being a cheerleader and she's in the bleachers.
4. Brad Paisley - "Little Moments" (2003)
#2 Hot Country Songs, #35 Hot 100
Brad Paisley's two most reliable kinds of singles are shamelessly loving odes to his wife and playfully clever uptempo tracks that border on novelty songs. "Little Moments" is the one song that successfully splits the difference and balance Paisley's wit and sentimentality in equal doses.
5. Toby Keith - "I Love This Bar" (2003)
#1 Hot Country Songs, #26 Hot 100
It's a shame that Toby Keith decided to write songs like "Courtesy of the Red, White and Blue" and "American Soldier" and become Nashville's right wing asshole poster boy of the George W. Bush era, because 95% of Toby Keith's singles are fucking bangers. It's funny how he sang "we like to drink our beer from a mason jar" about 5 minutes before that was considered more of a coastal hipster thing than a redneck thing.
6. Big & Rich - "Save A Horse (Ride A Cowboy)" (2004)
#11 Hot Country Songs, #56 Hot 100
Seeing this video on CMT one day was a really memorable moment, on par with seeing My Chemical Romance on MTV for the first time the same year. Big & Rich's campy irreverent hick hop turned out to be kind of a fleeting moment in the mainstream country zeitgeist, but "Save A Horse" is a lot better than most of the stuff it foreshadowed, from "Honky Tonk Badonkadonk" to 2010s bro country. And there are dozens of nerds who are still mad at Chuck Eddy for convincing them to buy an actual country album.
7. Rascal Flatts - "These Days" (2002)
#1 Hot Country Songs, #23 Hot 100
I was a little salty last year when a rapper went viral singing this song in a ski mask and inserting references to "the trap" into the lyrics, because I really do unironically love this song and always have.
8. Little Big Town - "Boondocks" (2005)
#9 Hot Country Songs, #46 Hot 100
Little Big Town didn't become reliable hitmakers until the 2010s, but "Boondocks" was a pretty big signature song that kept them afloat through their early years, and it remains maybe the best harmony showcase for all four members of the group.
9. The Chicks - "Goodbye Earl" (2000)
#13 Hot Country Songs, #19 Hot 100
I can appreciate the symbolic power of the Dixie Chicks dropping the first half of their name last year, but it does make me kind of sad because it obscures the Little Feat-inspired origin of the name. Veteran songwriter Dennis Linde had been marking references to a character named Earl in hits by Sammy Kershaw and others for years, and "Goodbye Earl" as a playful meta way for him to kill off the Earl character and no longer feature him in songs. Instead, Earl gained a whole new degree of immortality when a group on the cusp of superstardom covered the song.
10. Miranda Lambert - "Gunpowder & Lead" (2008)
#7 Hot Country Songs, #52 Hot 100
There's a long tradition of country songs where an abusive husband gets lethal comeuppance, and Miranda Lambert's early career highlight "Gunpowder & Lead" is in the more righteous and somber tradition than the more playful approach of "Goodbye Earl," but both are great songs.
11. Carrie Underwood - "Before He Cheats" (2006)
#1 Hot Country Songs, #8 Hot 100
Carrie Underwood's just defacing a car in "Before He Cheats," not murdering anyone, but still: the 2000s were a good decade for country songs about women getting revenge.
12. Montgomery Gentry - "My Town" (2002)
#5 Hot Country Songs, #40 Hot 100
Duo acts were commonplace in pop music a few decades ago, but they've remained a uniquely resilient staple of country music, from Brooks & Dunn to Florida Georgia. And many of those duos seemed to come together when two singers had trouble finding success as solo artists, including Troy Gentry and Eddie Montgomery, whose younger brother John Michael Montgomery was a multi-platinum star in the '90s. Neither of them were powerhouse singers but they had a good dynamic together, and had a great run of singles including "Hell Yeah" and "If You Ever Stop Loving Me" before Troy Gentry's death in a helicopter crash in 2017.
13. Shania Twain - "Up!" (2003)
#12 Hot Country Songs, #63 Hot 100
Between 1995 and 2002, Shania Twain released three of the biggest-selling country albums of all time, each of them moving over 10 million units, and then that remarkable run quietly ended: she took time off to deal with health issues, she divorced her songwriting partner and producer Mutt Lange, and she didn't release an album for nearly 15 years. Up! was the last and smallest behemoth of the Twain/Lange trilogy, but it might actually be my favorite, it takes their bright and bouncy aesthetic to an absurd new extreme, it actually sounds like an album where 9 of the song titles have exclamation points.
14. Terri Clark - "I Just Wanna Be Mad"
#2 Hot Country Songs, #27 Hot 100
Canada is full of country singers with its own scene and its own radio charts, as well as trailblazers like Hank Snow and Anne Murray, but outside of Shania Twain, relatively few modern acts have really had major success in America. Alberta's Terri Clark, however, had a pretty good run of platinum albums and radio hits in the '90s and early 2000s. Clark wrote most of her own hits with a great observational eye in the lyrics, but her biggest Hot 100 hit fell into her lap after Sara Evans made the mistake of passing on it.
15. Brad Paisley - "Alcohol" (2005)
#4 Hot Country Songs, #28 Hot 100
On one level, "Alcohol" is just a goofy, fun country song to hoist a beer or throw back a shot to. But Paisley is one of modern Nashville's more conceptual writers, and he sings the entire song from the perspective of the concept of alcohol itself, getting a little philosophical with lyrics like "I am medicine and I am poison" before hitting the punchlines ("You had some of the best times you'll never remember with me").
16. Dierks Bentley - "Lot Of Leavin' Left To Do" (2005)
#3 Hot Country Songs, #47 Hot 100
I grew up reading about Dierks Bentley's holistic detective agency, and it surprised me when he embarked on a successful career as a country singer. He has a certain plainspoken charm that helps put his songs over even when I wonder if they'd be better served by a more capable singer, and "Lot Of Leavin' To Do" is the most traditional of his hits, in a good way.
17. Toby Keith - "God Love Her" (2009)
#1 Hot Country Songs, #36 Hot 100
I don't know if this is one of Toby Keith's very best songs or if he just manages to elevate the cliche-ridden tale with the sheer force of his big resonant growl, but I love that last chorus with the breakdown when he hits the word "motorcycle."
18. Lee Ann Womack featuring Sons of the Desert - "I Hope You Dance" (2000)
#1 Hot Country Songs, #14 Hot 100
"I Hope You Dance" is one of those incredibly sappy crossover hits that was just everywhere, but I think its success was deserved, that lyric and that melody really work. The backing vocals were by Sons Of The Desert, a group that had just lost the race to make their version of "Goodbye Earl" a hit before the Dixie Chicks. Oddly, two members of Sons Of The Desert are brothers named Womack but they have no relation to Lee Ann.
19. Eric Church - "Hell On The Heart" (2009)
#10 Hot Country Songs, #67 Hot 100
Eric Church was my favorite country artist of the 2010s, and he didn't really hit the big time until 2011's Chief. But his excellent first two albums put him on the map with a series of minor hits, the best of which, "Hell On The Heart," did a good job of displaying the sound Church's producer Jay Joyce would soon be supplying to a number of other major artists.
20. Gretchen Wilson - "Redneck Woman" (2004)
#1 Hot Country Songs, #22 Hot 100
When it briefly felt like Big & Rich's MuzikMafia had taken over country music, all of that had to do with Gretchen Wilson's quintuple platinum debut album and its lead single co-written by John Rich. And her win at the American Music Awards made her the first of many artists to receive the ire of Kanye West when an awards show didn't go the way he wanted it to.
21. Taylor Swift - "Our Song" (2007)
#1 Hot Country Songs, #16 Hot 100
"Our Song" is the definitive Taylor Swift country hit, her first #1 on any chart and her biggest song on country radio that didn't really cross over to pop. It's also all of her early songs in a nutshell, all the infatuation and overthinking and looking at her relationships through the lens of music.
22. Gary Allan - "Watching Airplanes" (2007)
#2 Hot Country Songs, #43 Hot 100
In a pretty manicured era of country music, Gary Allan stood out with his raspy voice and soulful songs that seemed to carry the weight of a hard life that included his wife's suicide. "Watching Airplanes" is one of those songs where it's hard to imagine any of Allan's contemporaries pulling it off with the same gravitas, and that string arrangement is just killer.
23. Faith Hill - "Mississippi Girl" (2005)
#1 Hot Country Songs, #29 Hot 100
Faith Hill had been a multi-platinum star since 1993, but after Shania Twain redefined the possibilities of how many records a female country singer could sell in the ensuing years, it kinda felt like Hill spent a while playing catch up and making her music as crossover-friendly as possible. The John Rich-penned "Mississippi Girl" was a pretty calculated song to kick off her return to country music, but I have to admit, I just like it more than her pop material.
24. Luke Bryan - "All My Friends Say" (2007)
#5 Hot Country Songs, #59 Hot 100
Luke Bryan was, not counting Taylor's crossover-heavy work, the biggest country artist of the 2010s, absolutely huge and inescapable, and I usually changed the station when I heard his Jim Nabors honk of a voice on the radio. But one day I heard his debut single and realized that I really like it, even if it was all downhill from there.
25. Kenny Chesney - "There Goes My Life" (2003)
#1 Hot Country Songs, #29 Hot 100
Kenny Chesney is another ubiquitous superstar that I have pretty mixed feelings about, particularly when he's singing his "no shoes nation" beach bum anthems. But he can really pull on the heartstrings with a sentimental ballad when he wants to.
26. The Chicks - "Cowboy Take Me Away" (2000)
#1 Hot Country Songs, #27 Hot 100
"Goodbye Earl" was a B-side when DJs started to play the song and campaign for a single release of its own, but the A-side, "Cowboy Take Me Away," was a major hit in its own right and another one of the fka Dixie Chicks' best.
27. Toby Keith - "My List" (2002)
#1 Hot Country Songs, #26 Hot 100
"My List' is one of Toby Keith's few major hits that he didn't write, and it's a lot gentler than his usual fare. But it's a well written lyric and he sounds comfortable summoning a familial warmth that he otherwise doesn't often have much use for.
28. Brad Paisley f/ Alison Krauss - "Whiskey Lullaby" (2004)
#3 Hot Country Songs, #41 Hot 100
"Whiskey Lullaby" is one of Brad Paisley's few major hits that he didn't write, and it has a darkness and drama to it that's rarely found in his own compositions. But he summoned everything he had as a vocalist and an arranger as well as the perfect duet partner to bring to life songwriter Jon Randall's chilling autobiographical song about alcoholic self-destruction.
29. Josh Turner - "Long Black Train" (2003)
#13 Hot Country Songs, #72 Hot 100
Country's gospel roots still occasionally shine through in uplifting, inspirational ballads with Christian themes, but "Long Black Train" was the rare hit with a little old testament fear of the temptations of the Devil. And I don't think anyone else could've made that song go mainstream but someone like Josh Turner, movie star handsome with one of the deepest, most somber voices Nashville had heard since Johnny Cash.
30. Dolly Parton - "Better Get To Livin'" (2007)
#48 Hot Country Songs
Dolly Parton's legacy, in country music and in pop culture in general, seems to loom even larger now than it did at the height of her commercial success, and she's recorded 10 albums in the 20th century. But the only time in the last two decades that she really tried to play the game and cater to Nashville, with 2007's Backwoods Barbie, country radio more or less passed on a pretty excellent attempt at a comeback single. Still, she did get one more #1 with her Brad Paisley duet "When I Get Where I'm Goin'" in 2005.
31. Jo Dee Messina - "That's The Way" (2000)
#1 Hot Country Songs, #25 Hot 100
Artists on this list have come from all over the place, but Massachusetts native Jo Dee Messina is I'm pretty sure the only country singer from New England on here. The Tim McGraw-produced "That's The Way" was her highest charting Hot 100 song and got her first Grammy nomination, and it has the same slick sheen as a lot of pop country from the turn of the century but a nice dynamic rhythm section really livens it up.
32. Joe Diffie - "It's Always Somethin'" (2000)
#5 Hot Country Songs, #57 Hot 100
I didn't really check out Joe Diffie's music and realize how much I like it until last year when he sadly became one of the first notable musicians to die of COVID-19. "It's Always Somethin'" was one of the last radio hits he had while his '90s career peak was winding down, although Jo Dee Messina took a cover of Diffie's album track "My Give A Damn's Busted" to #1 a few years later.
33. Garth Brooks - "Wrapped Up In You" (2001)
#5 Hot Country Songs, #46 Hot 100
Scarecrow was the last album Garth Brooks released before his temporary retirement to focus on raising his kids, and kind of a rootsy back-to-basics record after the infamous Chris Gaines experiment. It feels like a forgotten chapter of his enormously successful career now, but "Wrapped Up In You" holds up as a pretty lovely little song.
34. Carrie Underwood - "Jesus, Take The Wheel" (2005)
#1 Hot Country Songs, #20 Hot 100
Like other early "American Idol" champions, Carrie Underwood went straight to #1 with her debut single, but since it was pre-written for whoever won the season, it didn't have a trace of the first country "Idol" winner's actual musical identity in it. But she quickly remedied that situation with her next single, and in the end it was clear which song Carrie Underwood built her career on: "Inside Your Heaven," which I wouldn't be able to hum at this point, stalled at gold certification, while "Jesus, Take The Wheel" eventually went triple platinum.
35. George Strait - "She'll Leave You With A Smile" (2002)
#1 Hot Country Songs, #23 Hot 100
"She'll Leave You With A Smile" was George Strait's 50th #1 country single, as well as his biggest Hot 100 hit. And it's a reminder of how many hundreds of songs he had to record to get to that milestone that it was not even his first "She'll Leave You With A Smile," he released a completely different song with that title by different writers in 1997. They're both good but I think the right one was a hit.
36. Tim McGraw - "Unbroken" (2002)
#1 Hot Country Songs, #26 Hot 100
I used to vaguely regard Tim McGraw as one of the best modern Nashville stars, but at some point I started to find his delivery really cloying, and now I reach for the dial pretty fast if I hear "My Next Thirty Years" or "Real Good Man" or even "Live Like You Were Dying." But out of his two dozen #1s, "Unbroken" is a relatively forgotten one that I really like, feels a little more lively and less saccharine than his biggest songs.
37. Taylor Swift - "Tim McGraw" (2006)
#6 Hot Country Songs, #40 Hot 100
It's been a long time since she needed to trade on anyone else's name, but Taylor Swift got a little help from the name recognition of at the time probably the biggest star in country to get her debut single on the radio. Co-written by Liz Rose (who herself had written a Tim McGraw song, 2002's "All We Ever Find"), "Tim McGraw" is kind of like a lesser "Our Song" where Taylor and the boy actually do have a song (apparently her favorite McGraw song that she had in mind was 2004's "Can't Tell Me Nothin'," which is kind of amusing since Kanye West had a hit by that same title).
38. Martina McBride - "Anyway" (2006)
#5 Hot Country Songs, #32 Hot 100
It kind of cracks me up how much this is the same song as "Do It Anyway" by Ben Folds Five, but slower and more serious, but I like both songs a lot.
39. Toby Keith - "How Do You Like Me Now?!" (2000)
#1 Hot Country Songs, #31 Hot 100
Toby Keith became a crossover star with bumper sticker-ready songs like "I Wanna Talk About Me" and "Who's Your Daddy?" that transformed him from a relatively normal machocountry singer to some kind of strutting Johnny Bravo-style caricature of raging id. And "How Do You Like Me Now?!" is by far the best of those, the one that gives the Toby Keith character an origin story and some tender verses to launch the big triumphant chorus out of.
40. Reba McEntire - "Somebody" (2004)
#1 Hot Country Songs, #35 Hot 100
Credit goes to Reba McEntire for continuing to release music and rack up radio hits the entire time she was starring in her eponymous sitcom for 6 seasons, she had a real multimedia empire going there. And "Somebody" is one of those songs that really deploys the power of her voice perfectly, that big ascending melody on the chorus has some beautiful harmonies.
41. The Chicks - "Not Ready To Make Nice" (2006)
#36 Hot Country Songs, #4 Hot 100
The no-longer-Dixie Chicks came back swinging with the perfect musical statement after the enormous backlash to their comments about that sack of shit George W. Bush. "Not Ready To Make Nice" was a triumphant in every sense, critically and on the pop charts and at the Grammys, except at country radio, where it was received tepidly. Still, #36 ain't bad considering that many stations outright boycotted the group.
42. Shooter Jennings featuring George Jones - "4th of July" (2005)
#29 Hot Country Songs
County tends to foster 2nd generation stars a little more readily than other genres, from Hank Jr. to Lukas Nelson, and a couple years after Waylon Jennings passed, his youngest son launched a career that's included some great solo albums and some Grammy-winning production work. Lots of country singers like to reference George Jones, but it probably helps to be the son of another legend to get Jones himself popping up singing a few bars of "He Stopped Loving Her Today" on your debut single.
43. Blake Shelton - "Some Beach" (2004)
#1 Hot Country Songs, #28 Hot 100
Before he was on "The Voice" and the cover of People and in relationships with two famous blondes, Blake Shelton was a C-list country singer with the worst mullet in Nashville. But I have a soft spot for the first song I heard by him, which felt like kind of a dry satire of the beach bum anthems that were taking over country radio at the time, with Shelton (in both the song and the video) dreaming of a tropical vacation while landlocked in an unpleasant workaday world.
44. Billy Currington - "Good Directions" (2006)
#1 Hot Country Songs, #42 Hot 100
A few months before Luke Bryan started making hits of his own, he wrote his first #1 for Billy Currington, a charming little story song about romance and turnips.
45. Cyndi Thomson - "What I Really Meant To Say" (2001)
#1 Hot Country Songs, #26 Hot 100
It doesn't feel like there are a lot of one hit wonders in modern country music -- the radio industry is so regimented and engineered to get established stars to #1 with almost every single that new artists rarely get there unless they're being prepped to return there and become a new A-lister. But Cyndi Thomson really just had the one big hit, the lovely Celtic-tinged ballad "What I Really Meant To Say," and then her next two singles missed the top 20 and she left the music industry for a few years and never released a second album. She did, however, co-write a Gary Allan hit a few years later.
46. Jessica Andrews - "Who I Am" (2000)
#1 Hot Country Songs, #28 Hot 100
Jessica Andrews is a little less strictly speaking a one hit wonder -- she released three albums and put almost a dozen singles on the charts, but "Who I Am" was far and away the biggest of them. She sang "if I never win a Grammy, I'm gonna be just fine," so I guess she's alright because she never did.
47. Brad Paisley - "Me Neither" (2000)
#18 Hot Country Songs, #85 Hot 100
Brad Paisley had already started to score hits when he released "Me Neither" but it was his last miss for a long time -- his next 27 singles peaked at #7 or higher, most of them #1s. It's one of my favorite Paisley singles, though, a fast and sharp-witted little dynamo of a song.
48. Little Big Town - "Good As Gone" (2006)
#18 Hot Country Songs
Little Big Town had a dry spell for a few years where they struggled to repeat the success of "Boondocks." But one of those singles that missed foreshadowed how they'd find their groove later, by letting Karen Fairchild's smokey and dramatic voice take center stage.
49. Sugarland - "Something More" (2005)
#2 Hot Country Songs, #35 Hot 100
I'm surprised Jennifer Nettles didn't have a big solo career because she really had a star quality that powered Sugarland's string of hits, a lot of people could've made this song big but I don't know if a lot of her contemporaries would've belted out that hook with the same force.
50. Toby Keith - "As Good As I Once Was" (2005)
#1 Hot Country Songs, #28 Hot 100
Toby Keith was a late bloomer who started releasing albums in his 30s and reached his commercial peak in his 40s. So while this playful song about his body starting to give out on him was probably pretty true to life, he was right in his prime artistically, consistently cranking out these entertaining but well crafted songs that almost always shot to #1.
This entry was posted
on Thursday, April 01, 2021 at 8:00 AM.
You can skip to the end and leave a response.
Post a Comment