A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #450-#441

The best entries in this run come from the slick countrypolitan era.  The backside of the seventies, if you will.


John Conlee, “Backside of Thirty”

#1 | 1979

JK: I can recall hearing this single as a recurrent maybe once, ever, and what a shame that is. The production is badly dated, like much of its era, but when a song and performance are this solid, they can overcome some chintzy excesses. About Right

ZK: I think the slightly syrupy production often dates Conlee’s records for me – especially here, where the tones feel a bit too bright for the subject matter – but he’s one of the most underrated artists of his era. Like Kevin says, the songwriting here is killer. Too High 

KJC: John Conlee kicked his career off with a string of instant classics, and this one might be the best of his entire catalog.  His songwriting does some of the heavy lifting here – “I skipped work last Friday to drink this month’s rent” says more in one line than most songs do in their entirety – but it’s his wailing vocal that brings it all home.  About Right



Kenny Chesney, “Summertime”

#1 | 2006

ZK: Oof. According to the folks at Sirius, This interchangeable tune is supposedly better than both “Anything But Mine” and “You & Tequila.” 

It’s not. So Wrong (Doesn’t Belong)

KJC: I’ll stick to DJ Jazzy Jeff and the Fresh Prince, thank you very much.  Chesney’s summer anthems make me long for the fall.  So Wrong (Doesn’t Belong)

JK: This song is a great example of songwriters who don’t understand the natural meter of language: The melody lifts on the final syllable, “Summertime,” in a way that is not how native English speakers actually pronounce the word. And it drives me up the fucking wall. So Wrong (Doesn’t Belong)



Restless Heart, “Why Does it Have to Be (Wrong or Right)”

#1 | 1987

KJC:  I mean, it’s fine, but this particular sound of Restless Heart has already appeared twice on the list, and with better songs to boot.  Their next and final entry is from the “No Larry Stewart years,” and they missed an opportunity to include his last big hit with the group, which has bluegrass-flavored harmonies and a completely different sound.  Swap this one out for “You Can Depend On Me.”  So Wrong (This Song)  

JK: Maybe it’s the amount of recurrent play it’s received on my local stations, but this is one of the singles of its era that has never really gone away. And I get it: It’s a little slick, to be sure, but the construction on this hit is just flawless in terms of its melody and how the interplay between the two lead vocal tracks reflect the tension of the song. This is probably the only single of theirs that I would absolutely have included. About Right

ZK: I can’t with that cluttered ’80s production and oversold performance. I got a headache from revisiting it. And … now it’s going to be stuck in my head all day. So Wrong (Doesn’t Belong)



George Strait, “Carrying Your Love With Me”

#1 | 1997

KJC:  I remember how huge of a hit this was.  He was so hot at this point that his clip for the song, which just alternated footage of him singing in an empty auditorium and him walking down a highway, earned a CMA nomination for Music Video of the Year.  Oddly enough, the best single from the same album is the only one that didn’t go #1, but I’d change this out for “Today My World Slipped Away” in a heartbeat.  So Wrong (This Song)

ZK: At this point, just wake me when we get to “Give It Away,” Strait’s next entry, and the first selection of his in a while that will make sense to me. Too High 

JK: One of Strait’s most massive hits, and one of his smoothest. Not necessarily one of his best, but it’s also a good exemplar of his 90s run. Too High



Lee Brice, “I Drive Your Truck”

#6 | 2012

ZK: Of the many, many Lee Brice inclusions here, this is one I totally support. About Right 

KJC:  A gorgeous sentiment, and if the past decade is going to be in the top 500 at all, this is one of the few hits that can justify the positioning.  About Right

JK: A song so well-executed that any of the men of this era could have had a hit with it. Which is to say that I don’t particularly get Brice, specifically, but this is easily his bid for immortality. About Right



Tom T. Hall, “Faster Horses (The Cowboy & The Poet)”

#1 | 1976

KJC:  I love that the seventies were open enough for an oddity like this to top the charts.  A fantastic record worthy of this ranking.  About Right

JK: I love this record. I love that country music used to allow records like this to be successful. How many great records from the last two decades– I’m looking right at you, Laura Bell Bundy’s “Giddy On Up”– would be on this list if radio hadn’t decided that it would no longer play these kinds of off-kilter singles. About Right

ZK: How the hell is “I Like Beer” just ahead of this? God, the production on this is so warped and weirdly wonderful, and it suits the ironic life advice quite well. Swap its placement with the aforementioned song, and we’d be getting somewhere. Too Low 



Luke Bryan, “I Don’t Want This Night to End”

#1 | 2011

JK: Bryan has entirely too many songs exactly like this, and if any of them have to be included, “Country Girl (Shake It For Me)” is the template for the rest. Leave it at that one and cut this. So Wrong (Doesn’t Belong)

ZK: Of all of Luke Bryan’s nighttime escapades – because there’s a lot of them, most of which are interchangeable anyway – this one kinda-sorta nails the sweeping rush of young love in the production. Which is to say that, even in 2011, Bryan was too old to be singing this. So Wrong (Doesn’t Belong)

KJC:  He’s one of the only guys of his era that can actually sing. I just wish he had better material.  So Wrong (Doesn’t Belong)



Joe Diffie, “Pickup Man”

#1 | 1994

ZK: The folks at Sirius really think this is the best Joe Diffie song. “Home,” “Ships That Don’t Come In,” “A Night To Remember” – good Lord, none of these tracks made the cut. I wouldn’t have even minded seeing the weird-ass “Third Rock From The Sun” this high. I might have used to this help kick off the list, but only if those others were included. So Wrong (This Song)

KJC: I always loved how this song was a sly wink to Diffie’s personal life at the time (“I met all my wives in traffic jams.”) This was his signature hit, and did more than perhaps any other to cement his reputation at the time as “Joe Ditty.”  Zack already listed the songs that should be higher than this, but I can’t imagine the list without it.  Too High

JK: I agree that “A Pickup Man” just has to be here: It highlights the relative artlessness of things like Chesney’s “She Thinks My Tractor’s Sexy” or Jerrod Neimann’s career-killing “Donkey.” But Diffie’s ballads should be here, too, and this entry is entirely Too High.



Crystal Gayle, “Don’t it Make My Brown Eyes Blue”

#1 | 1977

KJC:  Cosmopolitan country pop at its best, and one of those rare songs from that era that broke into the national consciousness.  Everybody knew this song.  I’m surprised it isn’t higher.  Too Low

JK: Gayle at her melodramatic finest. Just an exquisite record that sounds as classy today as it did more than forty years ago. Too Low

ZK: I wouldn’t have quibbled with a top 100 placement for this one. I could listen to that piano riff all day. Too Low 



Tim McGraw, “My Next Thirty Years”

#1 | 2000

JK: McGraw is wildly over-represented on this list; this is one of his better entries, but this is not in any way better or more significant than “Jolene.” Too High

ZK: This list is going to begin and end with a song that’s a bit too syrupy for me. It’s a credit to Tim McGraw’s skill as an interpreter, though, that he’s able to keep this grounded and make those promises he discusses not feel like empty ones. Too High 

KJC:  I can’t argue with this one being included.  It’s a great crossroads of life song centered around a milestone that gets a lot less attention than its 21 and 40 counterparts.  He’s as perfect a fit for a Phil Vassar lyric and melody as Jo Dee Messina is. It’s just not one of the handful of McGraw singles that belong in the top 500.  Too High


Previous: #460-#451 | Next:  #440-#431



  1. “I Drive Your Truck” is a good enough song, but just a little too High.
    I was never really impressed with “Carryin’ Your Love With Me.” Its just really bland IMO.
    “Pickup Man should be a little higher.
    “I agree with KJC: swap the Restless Heart song for “You can depend On Me” and move that song up higher

  2. I get the sense that the people who made this list are young and don’t know the history of country music. They seem to know of earlier songs but not the popularity or impact. That is the only way to explain the Crystal Gayle placement.

    I agree with Zack, I would not argue for this song as a top 100. It was a huge song and was well known outside of country radio.

  3. Favorites in this group are the Crystal Gayle and Tim McGraw songs.

    Don’t care much for Diffey’s “Pickup Man” but I agree w ZK on “Ships That Don’t Come In”. Love that song.

    Re Lee Brice, I like the “I Drive Your Truck” lyrics but would rather have a better vocalist like Collin Raye. I like Brice on “A Woman Like You”.

  4. “Faster Horses” is an off-beat classic that could easily be 200 places higher. Tom T was at his peak during my college years and I really looked forward to each of his new album releases because of the quality of Hall’s “slices of life” approach to story telling. Since Hall, Haggard, Pride, Lynn, Jones and Owens were issuing multiple albums annually, they contributed greatly to me being broke most of the time.

    “Don’t It Make my Brown Eyes Blue” belongs in the top 200

  5. Crystal Gayle is one of my most favorite artists from the countrypolitan/Urban Cowboy late 70’s and early 80’s era. Love her classy version of contemporary country! I really wish she was better represented on this list, and her signature song should be much higher up than this. That opening piano alone puts a smile on my face every time. My other favorites of hers include “Wrong Road Again,” “I’ll Get Over You,” “Talking In Your Sleep,” “It’s Like We Never Said Goodbye,” “Why Have You Left The One You Left Me For,” “The Sound Of Goodbye,” “The Blue Side,” “Too Many Lovers,” “Baby What About You,” “Our Love Is On The Faultline,” “Nobody Wants To Be Alone,” “Straight To The Heart,” and many more I’m sure I’m forgetting.

    “Carrying Your Love With Me” is also not one of my top favorites from George (perhaps maybe because it’s been played much more than a lot of his others), but it’s still a very enjoyable listen, and it takes me back to a much better time and place these days. That and because it’s one of his bigger hits from the 90’s, I’d be willing to give it a spot on this list. Kevin’s comment on the music video definitely got a laugh from me, though! I also agree that “Today My World Slipped Away” deserved a spot here. Also personally love “Round About Way.”

    Sigh…it continues to frustrate me that Joe Diffie is known mostly for his novelty songs today, while the majority of his ballads seem forgotten. “Pick Up Man” does deserve to be here, and Joe was one who could actually pull off most of these type of songs because he had the charm and personality that fits them well, imo. That said, I can’t help but wish he was also being represented by songs like “Home,” “If You Want Me To,” “Is It Cold In Here,” “Ships That Don’t Come In,” “So Help Me Girl,” and “A Night To Remember.” He was too good at the ballads, as well, for them to be ignored. “If The Devil Danced In Empty Pockets” is another one of his lighthearted songs I wouldn’t have minded seeing here, too.

    Always really liked Restless Heart’s brand of contemporary country from the 80’s and early 90’s. “Why Does It Have To Be” was always an enjoyable listen for me, and I’ll gladly jam to it over any bro-country tune any day, dated 80’s production and all. I’m totally with Kevin on “You Can Depend On Me.” I absolutely love that song, and it brings back so many great childhood memories! Would’ve loved seeing it here. I’m guessing “When She Cries” is the next RH entry, which is fine with me. “Mending Fences” is another one of my favorites from the non-Larry Stewart years.

    As someone who has always been a Fall/Winter person and not a fan of Summer (I personally hate heat, humidity, sunburns, mosquitoes, etc.), mainstream country’s obsession with the hotter months in the last decade or so has been quite aggravating, especially when they even insist on shoving these “summer anthems” down our throats when it’s already Fall or Winter. I remember there were times when my dad and I were riding around in his car and “Summertime” came on, and it was already well into November or December. Any time that would happen, I’d roll my eyes, and say “Check your calendar, Kenny!”

    “My Next Thirty Years” is not one of my favorites from A Place In The Sun (I prefer “Please Remember Me” and “Some Things Never Change”), but it’s still a pretty solid track, nonetheless. I agree that it shouldn’t be this high. I actually remember back when both this and “Just Another Day In Paradise” were fighting for the number one spot on the charts, making Phil Vassar compete with himself, which I thought was kinda funny at the time.

    “I Drive Your Truck” is the only Lee Brice song that’s worth putting on the list, imo, and even then, I don’t think I’d have it this high.

  6. Yup, “I Drive Your Truck” definitely belongs on this list. It is one of very, very few songs from this decade I don’t turn up the iPod to drown out when they’re playing the mainstream country station at the local barbecue joint.

    Sigh. I feel the same way about Joe Diffie as I do Tracy Byrd — great voice wasted on novelty bullshit. “Pickup Man” was a fun song and all, but come on. (Along those same lines, Kevin, completely agreed on Luke Bryan.)

    That Tim McGraw album was really good, but “My Next Thirty Years” was not one of my favorites on it. I would rather have seen “She’ll Have You Back” or “Señorita Margarita” released as singles.

    “Backside of Thirty” has always been a favorite. Pretty much everything John Conlee sent to radio (with the exception of “I’m Only In It for the Love” and “Domestic Life”) was golden to me. My favorite from him has always been “Old School.”

  7. I have always been a big John Conlee fan but the songs I really like from him are “Miss Emily’s Picture” and “I Don’t Remember Loving You”, both songs it takes a special singer to be able to sell

  8. The Pistolero – I LOVE those two songs from A Place In The Sun. “Senorita Margarita” definitely should’ve been a single!

    I agree with Paul that I would’ve rather seen those two John Conlee songs here instead. Also love “Friday Night Blues” and “Old School.”

  9. Yup, those were my two favorite songs from the TM album. If you haven’t yet, Jamie, you should also check out the original “She’ll Have You Back,” recorded by its writer Deryl Dodd on his 1996 album One Ride in Vegas; it’s very good as well.

    Paul, those are two of my favorite Conlee songs as well. I was so glad to have found his out of print 20 Greatest Hits on eBay way back in the day with all those songs on it. (This was a couple of years before all those songs were reissued on the Classics album.)

  10. Oh, I really like Deryl Dodd! I have his first two albums, and they’re both great. Very underrated artist. Some of my favorites from him are “That’s How I Got To Memphis,” “A Bitter End,” “This Ol’ World (Keeps Turning On Me),” “It’s Only Cause You’re Lonely,” and “Somewhere Down The Road.” And yes, his version of “She’ll Have You Back” is really good, too!

  11. I’m a big fan of John Conlee as well – I could listen to those 3(!) Classics albums all day long – Backside of Thirty is one of my favourites, but I also really enjoy Before My Time, I Don’t Remember Loving You and Old School.

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