I’m often glad I first experienced Brad Paisley’s music in my childhood.
Because, really, while I can pinpoint several factors that contributed to my early love of the genre, I know he’s one artist who helped welcome me in with open arms, especially when he was seemingly everywhere in the 2000s. But, I also get the common criticisms levied against him – in that he’s flagrantly corny with his humor and overly sentimental with his romantic tracks. I don’t so much disagree as just … see and hear his style in a different light. Going back through his discography affirmed a few things for me. For one, he’s such an affable and charismatic performer, that his jokes often come across with a hint of honest innocence, and I can honestly say the same for his ballads, too. He’s a performer who could both expand his sound and include Little Jimmy Dickens and George Jones, among others, on album tracks of his and even co-write with Bill Anderson – and on more than one occasion.
Again, as a kid, at a time when I, like everyone else, saw the world with a lot more wonder and excitement, Paisley helped me hang on to that feeling as long as I could. Oh yeah, he’s also an amazing guitar player who could actually take artistic risks and have them pay off in spades, like 2008’s Play or even a few riskier single choices we’ll explore later.
But, if there’s one criticism against him I can’t disagree with, it’s for one particular song off of his 2013 Wheelhouse album. Yes, I know it gets brought up every time someone now mentions Paisley – it kind of has to – and I won’t delve into the controversy surrounding it again. But if we’re looking for the point where he went from being a blazing A-list star to barely scraping the top 20, it would be there. And that genuinely sucks, because I’d argue his last album, 2017’s Love & War, was a strong return to form, and that even Wheelhouse itself was a pretty good album minus that one song.
For where he is now … well, he’s released a few scattered singles that have been hit and miss, and he’s on the cusp of a slight rebound thanks to being featured in Jimmie Allen’s “Freedom Was a Highway.” But I can’t help but feel he’s become largely forgotten and misunderstood to time and deserves better, especially due to, again, his incredible 2000s run. That’s what you all are here for, so let’s get this rolling – a rundown of my 15 personal favorite songs by Brad Paisley. Feel free to share yours here or wherever else you can reach me.
No. 15, “Some Mistakes” (written by Brad Paisley and Tim Owens)
My first selection pretty much embodies everything I like about Brad Paisley that I noted in my introduction; he’s likable and pretty much elevates a simple love song on pure charisma and execution. It also helps that the production is equally light and bouncy with the gentle mandolin and dobro interplay in the low end that lends a subtle little melodic swell to the sentiment. And for a song about finding the courage to dive into a relationship and explore the possibilities, it’s got the same lighthearted innocence about it that I like about, say, Josh Turner’s “Would You Go With Me.” That’s a high compliment.
No. 14, “Officially Alive” (written by Brad Paisley)
Again, Wheelhouse the album wasn’t that bad, and the one risk that often got ignored when it was released was Paisley’s foray into more atmospheric production that lent itself well to soaring choruses and huge hooks. This is the first example we’ll explore for this list, an anthem to live in the moment that works off of primal swell and power alone, in my mind. Of course, it’s Paisley, so the title is a double entendre that also captures birth and literally being “officially alive,” but it’s also that last verse that gets me – where he addresses parenthood and how it’s not the hard living and personal risks that give life meaning, but rather knowing the impact you’ll leave behind for your loved ones … and the ones still to come.
No. 13, “Letter to Me” (written by Brad Paisley)
I sort of just wrote about this one, only I really didn’t, and for as much as I’m thankful to have experienced Paisley’s music in my childhood, I know this is a song that would have resonated even more for me if I had been a bit older when I first heard it. As it is, it’s still a great song, a letter to the past we all wish we could write to ourselves. Only, Paisley doesn’t advise his younger self to change his course so much as … not worry about it, and also take the time to appreciate it and the people around him along the way. Yes, it’s a familiar theme, but Paisley explores it such in a unique and personal way by eschewing any thoughts of regret or possibly doing things differently, that it becomes a nostalgia trip that isn’t so bad to indulge.
No. 12, “The Cigar Song” (written by Brad Paisley)
… I mean, I don’t know if it’s the best song ever about insurance fraud, but it’s certainly the best one I’ve ever heard – in country music or in general, not that I can think of many more I’ve heard anyway. I think I might have liked it even better if Paisley had gotten away with his scheme, but as it is, it’s still a nasty little song that’s brimming with some great one-liners. I’d describe Paisley’s approach to comedy as more akin to, say, Little Jimmy Dickens or Bill Anderson. But this is a slice of dark comedy in the vein of Roger Miller, and that’s the highest praise I can give it, I think. I often resort to calling songs I like great little slow burns, and I think describing this as such in a literal sense may be the most fitting way to end this blurb.
No. 11, “You’ll Never Leave Harlan Alive” (written by Darrell Scott)
If you’re sitting there wondering how I could name this my favorite Patty Loveless song and yet not even within my top ten favorite Paisley songs, it’s because I do think she has the ultimate version of it – yes, even above writer Darrell Scott’s version. Still, this is the first version I heard and fell in love with, and that’s why it’s worth highlighting again. If anything, it proved that Paisley could both write and pick great songs, and that there was always more to him than just his jokes.
No. 10, “Who Needs Pictures” (written by Brad Paisley, Chris DuBois, and Frank Rogers)
It’s rare that a song can sound so dated and yet so timely all at once. Even if the Kodak references here will likely go over some heads today, the sentiment of not needing pictures to capture a moment when memories are all that are needed to preserve the moment is one Paisley sells with affable conviction. Beyond sporting one of his best lyrical hooks, I think what helps keep the title track and first single from Paisley’s debut effort from falling into the same camp as a lot of power ballads that populated within country music around the late ‘90s is that, in the end, he loses his significant other and is now truly put to the test he set for himself. Predictable to a fault, sure, but still one that’s sad and that Paisley sells well regardless. Truly underrated, and a song that paved the way for so much more.
No. 9, “A Man Don’t Have to Die” (written by Rivers Rutherford, George Teren, and Josh Thompson)
Brad Paisley has a surprising amount of great songs in his discography that tackle religion and faith, and while tracks that are more distinctly his in “The Devil is Alive and Well” and “Those Crazy Christians” just missed the cut for this list, “A Man Don’t Have to Die” perhaps work best for its bluntness; first through the fantastically textured production that emphasizes the thicker strumming and solid bass line for a much more tempered, melancholic atmosphere, and then through the content. It comes from the perspective of the wayward sinner who has lost everything to alcoholism and divorce and won’t allow himself to get caught up in the religious fervor that often comes with living in a small town. To him, he’s already in Hell anyway and is only in attendance at church for a last ditch effort at salvation he knows will likely fail him anyway, because he’s already failed himself. Direct and straightforward, for sure, but also in a way where the point is made clearly by that first verse and everything afterward is sweet misery drenched in realism and regret.
No. 8, “I Wish You’d Stay” (written by Brad Paisley and Chris DuBois)
Damn it, Brad Paisley should not have made a country power ballad drenched in strings and piano flourishes work this damn well. Yet, he did. Again, he’s such a convincing performer of all varieties, so when he tries to sell the role of the displaced partner who has to watch his significant other leave town to chase her dreams, he’s able to conjure sympathy from the audience naturally. For as much power as there is in that hook, I think what works best about it is that, for one, Paisley isn’t trying to trap or stop her. He knows she has to do whatever it is she’s going to do, and if that means starting an entirely new life, he’s going to give her the space she needs to find herself. But that he still so desperately wants her to stay and knows it’s a plea for naught is what gives the song its potency in a way that can be powerful without being clingy, all the more evidenced by that smoldering outro.
No. 7, “American Flag on the Moon” (written by Brad Paisley)
Here’s the thing, I won’t deny that Paisley isn’t corny as a whole at points; I’d still just qualify it as endearing nonetheless, that’s all. This is another track here to work off pure earnestness, from the spacey production and echoing melodies that give it such a huge and hopeful swell, to the message that’s simply about daring to dream big – even if it extends to space-age optimism. If anything, it’s more timely now than it was when it was first released seven years ago. It’s also one of the very, very few tracks to implement a child’s choir and kind of make it work, if only to further inspire the next generation to fuel that inner fire and believe in … well, something.
No. 6, “Alcohol” (written by Brad Paisley)
… I mean, come on – Brad Paisley rips away the veneer from country music’s most popular song topic and completely flips it on its head by having him personify and sing from the perspective of the titular item; of course it’s one of his best songs. And while I could point out how this song excellently highlights the consequences of it without ever once condemning anyone or coming anywhere close to judgmental or preachy, and is, instead, meant to be just overblown in the best way possible while making fun of its audience, let’s face it – it’s that huge chorus and hook that cements it as a modern classic. And that’s before mentioning how Paisley rightly turns it into a bar sing-a-long by its end. Even the people I know who don’t quite like him like this song, and there’s a few good reasons for that.
No. 5, “Out in the Parking Lot” (written by Guy Clark and Darrell Scott)
As much as I do love Guy Clark’s take on what he once described as “the antithesis to ‘Boot Scootin’ Boogie’,” it comes alive here thanks to the buddy element and camaraderie established between Brad Paisley and Alan Jackson. Really, they’re two straight-laced performers themselves with an incredible eye for detail, hence why this anti-concert song that’s basically about watching everyone stumble around the parking lot during a concert – fueled by alcohol and whatever else is in their systems – has a lighthearted humor to it (whereas the original is more strangely melancholic). Either way, my God, there’s a strong element of truth to it that easily places me within that environment, and this song provides the sort of team-up I’m surprised we didn’t hear more of from these two specifically.
No. 4, “When I Get Where I’m Going” (feat. Dolly Parton) (written by Rivers Rutherford and George Teren)
As we begin to discuss the last few entries on this list, I know some of my personal top picks are among the more divisive ones in Paisley’s discography, especially depending on the audience. I do find that kind of ironic, given that I’d argue Paisley’s simplicity rang even louder than any supposed attempts at being spiritual or political, and that, if anything, his aim was always to connect rather than divide. What’s striking to me about the first entry within that category is that Paisley didn’t write it … and yet it sounds exactly like he could have. “When I Get Where I’m Going” captures the same playful innocence in its meditation on the peace that could potentially come with death without coming across as preachy. The strength has always came through in the humanity shown, along with hope for an afterlife that many of us would like to believe exists in some form. Really, though, if there’s an element that pushes it even further over the top, it’s that gentle dobro accompaniment, and it’s Dolly Parton’s angelic soprano providing a gorgeous counterbalance to Paisley’s plaintive tone and bright-eyed wonder. Beautiful stuff.
No. 3, “Welcome to the Future” (written by Brad Paisley and Chris DuBois)
I just talked about this song not too long ago, so to reiterate a few points: it’s huge and sweeping in its potency in the way Paisley’s best cuts are, complete with a relentlessly upbeat hook and optimistic outlook that’s a pure trademark of his career. Not quite his best reflection on the world around us – trust me, we’ll get to it – but it is the most daring, particularity for that final verse that’s meant to be uncomfortable yet emblematic of the work done and to be done. Again, I wouldn’t say Paisley has ever aimed to be particularly philosophical, but it is telling how much the subtext of his messages linger long after the songs they appear in end, hence why even the simplest statements can ring far louder than we can even imagine.
No. 2, “Southern Comfort Zone” (written by Brad Paisley, Chris DuBois, and Kelley Lovelace)
What I’ve always loved about Paisley’s more earnestly serious songs is his knack for making grand statements with simple language. “Southern Comfort Zone” is the other moment from Wheelhouse that I think ranks among his best, a huge blast of energy with several killer hooks attached to it that’s about leaning in to that fast-paced craziness by having him confront the world beyond him. Unlike the rural pride pandering that would – and continues to, unfortunately – plague so many country songs the year this song came out, this is a song where Paisley understands what it’s like to be an outsider and wants to establish a connection regardless. It’s a moment where country music went international, and in my mind, it doesn’t get enough credit for it. It would be my favorite Paisley song, if not for one more …
And before we get to that, let’s examine a few honorable mentions that just barely missed the cut for my list, in no particular order:
“Last Time For Everything” (written by Brad Paisley, Smith Ahnquist, Brent Anderson, Chris DuBois, and Mike Ryan)
“The Devil Is Alive and Well” (written by Brad Paisley, Robert Arthur, and Kenny Lewis)
“Time Well Wasted” (written by Ashley Gorley and Kelley Lovelace)
“I’m Gonna Miss Her” (written by Brad Paisley and Frank Rogers)
“Dying to See Her” feat. Bill Anderson (written by Brad Paisley and Bill Anderson)
“All You Really Need is Love” (written by Brad Paisley, Chris DuBois, and Frank Rogers)
“Without a Fight” (feat. Demi Lovato) (written by Brad Paisley, Kelley Lovelace, and Lee Thomas Miller)
Lastly, any instrumentals and Kung Pao Buckaroo skits, because, yeah, duh …
No. 1, “Whiskey Lullaby” (feat. Alison Krauss) (written by Bill Anderson and Jon Randall)
You know, my last two discussions were on songs deemed risky for Brad Paisley, and while that remains true from a cultural standpoint – especially given the time period in which they were released – I honestly think a song about a double suicide caused by whiskey is among the most daring releases in country music specifically, even given its history of indulgence with its alcohol. I know I’m not alone in thinking this is both Paisley and Alison Krauss’ best song, either (or in the latter artist’s case, at least among her best) – a pretty common opinion, actually, it seems. Before I even delve into the song itself, I can highlight so much it did right beyond it, like proving that Paisley was always worth more than just his jokes and that maybe his critics were wrong about him, and that recruiting Krauss to deliver one of her most haunting verses and vocals in general was absolutely the right call, especially with Dan Tyminski adding additional support.
Though both performers act as observers and storytellers here, there’s so much added weight in having each of them contribute a verse to the larger story. Which is to say that the song is, of course, exceptionally written, sketching the breaking point for each partner in the relationship and how their own unfortunate actions caused a domino effect that eventually led them back to each other … and hopefully to find a peace they couldn’t find on Earth, too. The production is sparse, carried only by faint touches of bass and dobro to highlight that stark and lonely contrast, but in a way it also does provide that needed sense of closure and peace by its end while also sounding utterly bleak and melancholic otherwise. Honestly, it’s so depressing and frank in what it’s going for, that I’m actually thankful the “la’s” can provide some semblance of peace and levity to this lullaby. These rankings don’t really matter, ultimately, but I don’t think it should come as a surprise that, to me, this is not only Paisley’s best song, but the absolute best song of the 2000s, and one of the finest in all of country music history.