A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #930-#921

NEW ORLEANS, UNITED STATES - APRIL 23: Willie Nelson performing at the New Orleans Jazz & Heritage Festival on April 23, 1999. (Photo by Clayton Call/Redferns)

Willie Nelson kicks off the next ten entries of this very long list.


Willie Nelson, “Last Thing I Needed First Thing This Morning”

#2 | 1982

JK: The number of pleasant surprises on this list is quite small, but this single by Willie Nelson certainly counts among them. I’ve always loved how utterly put-out Nelson sounds in his performance on this song. About Right

KJC: A breakup song put in the larger context of an already bad day, Nelson’s weary vocal is the perfect vehicle for the “You’ve got to be kidding me” sentiment of this underrated hit.  About Right


Keith Urban, “Kiss a Girl”

#3 | 2009

KJC:  A breezy summertime hit that is elevated by Urban’s enthusiastic vocal, “Kiss a Girl” gets the job done but isn’t nearly as compelling as his darker ballads that this list overlooks in favor of lightweight jams like this.  So Wrong (This Song)

JK: In the early-aughts, Keith Urban did uptempo pop-country as well or better than just about anyone in the genre, with an ear or a pen for quality material and a masterful way with both pop and country conventions. “Kiss a Girl” isn’t anywhere close to his best within the context of what he does well, and to think they ranked this higher than “Long Black Veil” is maddening. So Wrong (This Song)


Sawyer Brown, “Six Days On the Road”

#13 | 1997

JK: Like Shenandoah, Sawyer Brown never really got the credit they deserved in their own era, despite having some truly great material to their credit. And like Shenandoah, Sawyer Brown’s best material isn’t necessarily represented on this list. I’d have included all three of the singles Kevin lists below. So Wrong (This Song)

KJC:  Four songs on the list, and they’re all uptempo tracks.  Swap this one out for “The Walk,” “Cafe On the Corner,” or “All These Years,” please.  So Wrong (This Song)


Bobby Bare, “Drop Kick Me Jesus”

#17 | 1976

KJC:  Bobby Bare may be the most underappreciated artist in the Country Music Hall of Fame.  This track is a highlight from his wry and entertaining collection, The Winner and Other LosersAbout Right

JK: I love Bare and I love this single, in particular. Such a singular talent. About Right



Dixie Chicks, “Ready to Run”

#2 | 1999

JK: The pluck and sass was one of their trademarks, and the self-deprecating lyrics here played to their strengths. But let’s take just a second to point out that “Long Time Gone,” the best country single of the aughts bar none, isn’t on this list at all. About Right

KJC:  These gals were so good, they could make a song that works for the soundtrack of a film with as ridiculous as a concept as Runaway Bride, yet still stands on its own as a declaration of independence and youthful vitality.  About Right


Lady Antebellum, “Compass”

#6 | 2013

KJC: The first of eight songs from this popular aughts band, “Compass” is the sound of Mumford & Sons under the influence of Ambien.  So Wrong (Doesn’t Belong)

JK: The dullest act in popular music have, at most, two singles that belong in this conversation. This isn’t one of them. So Wrong (Doesn’t Belong)


Miranda Lambert & Carrie Underwood, “Somethin’ Bad”

#1 | 2014

JK: Underwood’s fanbase resents Lambert with a fiery passion, and Lambert’s fans are only slightly less toxic in return. Something that both fanbases seem to agree on, though, is that “Somethin’ Bad” is a wasted opportunity that is far beneath either woman’s respective talents. Hopefully, these two– who actually do seem to like and respect each other– record a better collaboration someday. So Wrong (This Song)

KJC:  A good enough collaboration, but the list would be stronger if Lambert’s “Little Red Wagon” and Underwood’s “Little Toy Guns” were included instead.  So Wrong (This Song)


Wynonna, “Tell Me Why”

#3 | 1993

KJC:  I’m happy they included a decent number of Wynonna’s solo hits.  This has a sixties pop feel to it that still sounds great today. About Right

JK: With her fearless approach to genre, Wynonna predicted Americana long before it was a thing. At least with my local radio stations, this scored a ton of airplay across formats, and it’s not hard to hear why. About Right


Alan Jackson, “Country Boy”

# 1 | 2008

KJC:  He’s done this type of song so many times, and I don’t think I’ve enjoyed it even once.  So Wrong (Doesn’t Belong)

JK: Jackson has one of the best ratios of quality hits of his era, but when he’s bad, he’s really, really, really bad. So Wrong (Doesn’t Belong)


Charlie Walker, “Pick Me Up On Your Way Down”

#2 | 1958

JK: An absolute classic single that, like so many on this list, is slighted in favor of recent bro and post-bro trash. Too Low

KJC:  Twin fiddles, pure twang, and the clever wordplay of a young Harlan Howard.  No complaints here. About Right

Previous: #940-#931  | Next: #920-#911


  1. Never was a fan of Sawyer Brown’s up-tempo stuff, with the exception of “Did it for Love” this song just doesn’t belong.
    Wynonna doesn’t belong on the list at all, especially when you consider some very good songs left off, that could replace it. There’s a song that isn’t even listed that I’d pu in the top 100 maybe top 50, but we’ll get to it later.
    “Compass” should be a little higher.

  2. I like the Willie Nelson, Sawyer Brown, and Dixie Chicks songs. “Pick Me Up On Your Way Down” is a classic in which I agree should be placed higher on the list. My biggest favorite here is “Tell Me Why” by Wynonna. By far, one of her best solo singles, imo. It still sounds great while going on a long drive.

    “Country Boy” is hands down one of the worst singles AJ ever released in his career, and I’m simply baffled that it even made the list. I shudder to think which of his much superior singles didn’t make it in favor of this one.

    “Kiss A Girl” is a harmless, lightweight tune, but I just don’t understand how it’s seemingly become one of his most popular songs out of all the singles he’s released. It just doesn’t hold up as well for me like “Somebody Like You,” or some of his other earlier singles. “But For The Grace Of God” better have made the list, if this was included.

    I used to like “Compass,” but it hasn’t aged too well for me these days.

    “Somethin’ Bad” is certainly fun, but not worthy of this list.

    I can’t believe that none of Sawyer Brown’s ballads made the list. Seriously, “All These Years” is not on here at all?!

  3. “Country Boy” isn’t great but an Alan song is always enjoyable.

    Any Dixie Chicks song is vastly overrated.

    This list of ten songs was a struggle for sure. “Something Bad” just sucked. “Kiss a Girl” is generic.

  4. Love the Chicks – especially their sassy songs. Agree w JK re “Long Time Gone”. Still like Wynonna too. “Tell Me Why” is good but not one of her best.

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