A Country Music Conversation: Sirius Top 1000 Country Songs of All Time, #520-#511

A few criminally underranked gems show up in this batch.



Dierks Bentley, “Lot of Leavin’ Left to Do”

#3 | 2005

JK: A fine enough radio hit, but Bentley could’ve been better represented by some of his lower-charting singles, too. Give me “Bourbon in Kentucky” or “Say You Do” or “Up On the Ridge,” instead. So Wrong (This Song)

KJC:  It was clear by this point that Bentley’s songcrafting skills were solid.  But they weren’t particularly compelling yet. Jonathan’s suggested replacements prove they eventually would be. So Wrong (This Song)

ZK: I’ve always loved the Waylon-esque groove and Bentley’s hangdog charisma on display here. An early hit that proved why he was one of the more interesting male artists to emerge in the 2000s. About Right



Freddie Hart, “Easy Loving”

#1 | 1971

KJC: A classic record that is definitive of its respective era.  Too Low

JK: Because I’m me, I actually prefer Kelly Hogan’s cover of this to Hart’s genre staple. But I’m certainly not going to argue against Hart’s rendition, either. In fact, this is far Too Low.

ZK: Freddie Hart is deeply under-appreciated as a whole, so yeah, it’s obviously Too Low. 



LeAnn Rimes, “Blue”

#10 | 1996

JK: Wildly overpraised in the way that child prodigies so often are, Rimes’ performance is an affectation. It’s an impressive affectation, to be sure, but it also doesn’t hint at how she’d re-emerge a decade later as one of her generation’s finest and most distinctive interpretive singers and a fascinating songwriter. The emotional depth of something like “Probably Wouldn’t Be This Way” or “What Have I Done” are better showcases for what she can do, but this single, a peculiar museum exhibit, belongs here, too. Too High

KJC:  Nothing Rimes would do for years after this would be as remotely interesting as “Blue.” It’s her only essential nineties single.  About Right

ZK: As Jonathan suggests, this seems to be a “love it or hate it” suggestion, where I happen to be of the former opinion. With that said, follow-up singles failed to establish her as a unique presence within the genre, and I would agree she got better with time. Too High 



Jake Owen, “The One That Got Away”

#7 | 2012

KJC:  Oh, the hundreds of songs that got away from this list because of entries like “The One That Got Away.”  Some of them by Owen himself, even.  So Wrong (This Song)

JK: Yeah, I’m still going to bat for the half verse he contributed to that gorgeous “Life In a Northern Town” cover with Sugarland and Little Big Town over this. So Wrong (This Song)

ZK: This is one of the most common song titles out there, and Owen’s charisma can’t save what is ultimately a lackluster song. So Wrong (This Song)



Tanya Tucker, “Would You Lay With Me (in a Field of Stone)”

#1 | 1974

JK: There absolutely are not 515 country songs better than this. My God. Too Low

KJC:  I’ve said it before and I’ll say it again. All of her Southern Gothic hits from the seventies belong on this list.  In fact, slip “Blood Red and Goin’ Down” into this slot and bump this one up a few notches.  Too Low

ZK: Sirius, you already pissed me off last time with the Kathy Mattea placement. Don’t start again. Too Low



Toby Keith, “Courtesy of the Red, White, and Blue (The Angry American)”

#1 | 2002

KJC: For the perversion of the Statue of Liberty alone, I’d kick it off the list.  But that’s the native New Yorker in me. I could also name a dozen Keith singles that I’d put on this list that didn’t make it.  But I don’t think you can tell the story of country music without its inclusion.  How on earth it’s ranked above “Where Were You (When the World Stop Turning),” I will never understand. Too High

JK: Had Keith couched this as an of-the-moment, reactionary statement and not an insistence that this kind of swinging-dick posturing is the only true expression of patriotism, his career would probably be regarded with a lot more grace, and our political discourse would not have been cheapened to the extent that it has been. On very broad impact alone, it probably has to be on here, but this ranking is Too High.

ZK: As someone who recently wrote about Alan Jackson’s “Where Were You (When The World Stopped Turning)” for this website, it’s fascinating seeing the parallels between that and other songs of the era like this or “Have You Forgotten.” Not that anger wasn’t an understandable emotion; it was, especially here. But this overblown declaration of patriotism only fed directly into the negative political stereotypes surrounding country music, when – as Jackson suggested – it could be a lot more nuanced and graceful than that. So Wrong (This Song)



Mary Chapin Carpenter, “Passionate Kisses”

#4 | 1992

JK: Hell of a juxtaposition between the previous entry and this one. How amazing would it have been if A-listers Score Top 5 Hits By Covering Lucinda Williams had become an actual trend. About Right

KJC: So little Chapin on this list that I’m a bit annoyed one of her slots is taken up by a cover.  But what a cover!  Country radio was so wide open by this point in the nineties that a Lucinda Williams song could go top five, just less than two years after Patty Loveless had her top ten hit streak broken by the underperformance of her brilliant take on “The Night’s Too Long.”  About Right

ZK: Just seeing the title has that hooked lodged in my brain. About Right



Faith Hill, “The Way You Love Me”

#1 | 2000

KJC: I love Faith Hill, but for me, her Breathe album was her artistic nadir, even if it resulted in her highest sales.  That album had two great singles, and while the title track was obviously included, this one should be swapped out for “If My Heart Had Wings,” which has the heart that this track is missing.  So Wrong (This Song)

JK: Hill turns in one of her most robotic performances– no two consecutive words of this sound like they were recorded in the same session– on a song so poorly written that the liner notes should have been written with chunky toddler crayons. Just awful. So Wrong (Doesn’t Belong)

ZK: I’m usually left resorting to a single word when referring to Hill’s output: “meh.” So Wrong (Doesn’t Belong)



Tyler Farr, “Redneck Crazy”

#2 | 2013

JK: The only upside here is that it inspired Millie Jackson’s cover version. So Wrong (Doesn’t Belong)

KJC:  Remember when country radio wouldn’t play “What’ll You Do About Me” and Doug Supernaw lost his first major label record deal largely because of that?  He’s got to be annoyed every time this comes on the radio. So Wrong (Doesn’t Belong)

ZK: Here’s the thing about “bro-country” – it’s a subgenre; not an immediate marker of quality. Sometimes those party songs were fun. This, however, shows why the trend was ultimately a black eye for the genre – a leering, miserable, misogynistic and downright creepy song reeking of entitlement. Jason Aldean is producing this guy’s records now, if that says anything. So Wrong (Doesn’t Belong)



Doug Stone, “Why Didn’t I Think of That”

#1 | 1993

KJC: Doug Stone’s material was too cute by half.  “Pine Box” belongs on here, as noted below, is a glaring omission, and arguably the only representation Stone needed on the list.  So Wrong (This Song)

JK: Cutesy and twee and it makes my diabetic pancreas hurt. “I’d Be Better Off in a Pine Box” should be ranked around here, if not even higher. So Wrong (This Song)

ZK: ’90s country, I love ya, but if you weren’t corny enough when you tried to turn dad jokes into songs, you certainly crossed the line with cheesy fluff like this. So Wrong (This Song)

Previous: #530-#521 | Next:  #510-#501


  1. Re. “Easy Loving”: And just for crossover chart trivia, this song got up fairly high on the overall Hot 100, #17 to be precise, in the fall of 1971–which meant that you could also hear it on pop radio alongside Rod Stewart (“Maggie Mae”), Cher (“Gypsys, Tramps, And Thieves”), and Isaac Hayes (“Theme From ‘Shaft'”), to name just three examples.

    Re. “Passionate Kisses”: A great example of why women were so important to country music in the 1990s, both for Lucinda Williams’ songwriting genius, and MCC’s folk/country/rock skills.

    Re. “Courtesy Of The Red, White, And Blue”: While it may have been understandable for us to have rage, anger, and a thirst for revenge in the wake of the seismic event of terror that 9/11 was, it is unfortunate that Toby Keith basically exploited that rage, and a blind form of patriotism that Samuel Johnson called “the last refuge of a scoundrel”, much more out of his own self-aggrandizement than any true love of country. And I say this unapologetically, being the son of a father who served with honor in Korea and Vietnam.

    Re. “Redneck Crazy”: The less said about that misogynistic Tyler Farr tripe, the better.

  2. I commented years ago that Tanya Tucker’s best singles were about as good as it ever gets – her early Southern Gothic singles include about six that should be in the top 300 at least

    “Easy Loving” could easily fit in the top 200

    I can think of several Doug Stone songs that belong on this list “(I’d Be Better Off In A) Pine Box” – yes but also “Fourteen Minutes Old” and “Jukebox With A Country Song”

    That Tyler Farr entry wouldn’t belong in a Top 5000 list

    If one wanted to include “Blue”, supposedly originally written for Patsy Cline, a good choice would have been the original recording by Kenny Roberts on Starday in 1967. Roberts was a unique performer and actually had a pair of million sellers during the late 1940s.

  3. @Erik – regarding your Samuel Johnson and “last refuge of a scoundrel” comment I give you
    Ambrose Bierce in his Devil’s Dictionary:
    PATRIOTISM, n. Combustible rubbish ready to the torch of any one ambitious to illuminate his name.
    In Dr. Johnson’s famous dictionary patriotism is defined as the last resort of a scoundrel. With all due respect to an enlightened but inferior lexicographer I beg to submit that it is the first.
    bonus definitions:
    PATRIOT, n. One to whom the interests of a part seem superior to those of the whole. The dupe of statesmen and the tool of conquerors.
    Politics – “A strife of interests masquerading as a contest of principles. The conduct of public affairs for private advantage”.

    I also don’t like the Angry American song with its boot in your ass attitude. Don’t know about TK’s motive. Agree w KJC that AJ’s “Where Were You” should be higher on the Sirius list. I have 16 TK songs in my i-tunes library. AA is not one of them and neither is get drunk & be somebody. I did like some of his early material.

    I liked JK’s comment about “swinging dick” posturing. Last time i heard that expression it was from a drill sergeant over 50 years ago.

  4. If I never hear “Redneck Crazy,” “Why Didnt I think of that,” or “Courtesy of the Red White and Blue,” It’ll be too soon

  5. I absolutely love “Passionate Kisses.” For me, it’s one of the ultimate feel good songs. Not to mention, it takes me back to simpler and happier times in my childhood. That chiming guitar alone always brings me joy when I hear it. :)

    Nice to see Doug Stone here again, but this is not one I would’ve chosen to represent him. Like many others have said, “Pine Box” definitely belongs here, and I agree with Paul on “A Jukebox With A Country Song.” I also wouldn’t have minded seeing “I Thought It Was You” or “Too Busy Being In Love.” Both “Why Didn’t I Think Of That” and “Different Light” seemed to be the only songs radio remembered from him for the longest time before dropping his music altogether, and now they’re predictably the only entries of his on this list. SMH

    The Dierks Bentley song is okay and I kinda liked it when it came out, but it got overplayed in my area. I also eventually grew tired of hearing that Waylon like beat, as it seemed like many other songs started using that same beat around the same time and got to be too cliched. I’d also go to bat for “Say You Do,” or “Bourbon In Kentucky.” Also love “Draw Me A Map.”

    Nostalgia for the early 00’s is pretty much one of the only reasons I enjoy the Faith Hill song, though I’d definitely take it over most of what’s been on the radio the last 10-15 years. Would’ve preferred seeing “Let Me Let Go” or “The Secret Of Life.”

    As I’ve said before, I consider Toby Keith’s downhill slide in quality to be after “Angry American.” That’s when I feel he started going overboard with the drinking and patriotic songs and overly macho stuff. I liked him much better when he still released songs like “Dream Walkin’,” “We Were In Love,” “Me Too,” “Does That Blue Moon Ever Shine On You,” “You Shouldn’t Kiss Me Like This,” and “My List.” I agree wholeheartedly with Zachary’s comparison between “Angry American” and “Where Were You.”

    Sigh….Why Tyler Farr even on this list?

  6. I like Doug Stone’s “How Do I Get Off the Moon” and “Nice Problem”.
    For Faith Hill, I agree w Jamie’s picks of “Let Me Let Go” and “Secret of Life”

  7. I think I’m pretty much a Doug Stone apologist too (and Tracy Byrd), as I like his voice and the majority of his singles. I especially enjoy his first three albums. I also like his 1999 comeback hit, “Make Up In Love.” For the record, I do also like “Why Didn’t I Think of That.” It’s just not one of my top picks from him. :)

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