It shouldn’t be this hard to write about my favorite Trisha Yearwood songs, and there shouldn’t be this many reasons for why it’s felt impossible to establish context as to why it’s been so difficult. Establishing her background as an artist? That’s easy. She’s a terrific singer who recorded some of the most notable songs of the decade. See? Easy, like I said.
But as I’ve said before, I didn’t grow up with ‘90s country. I grew up in the 2000s, when everyone’s biggest complaints about the genre were that it was no longer the ‘90s – ah, nostalgia. So, I can say that I experienced Yearwood’s music a bit differently than other fans. See, like contemporaries such as Alan Jackson, George Strait, Reba McEntire, and, yes, even husband Garth Brooks, Yearwood was one of the few artists from the previous decade to see success in the new one. It took a comeback following a messy entry into said century, but it happened, and I remember hits like “Georgia Rain” and “Heaven, Heartache & the Power of Love” before I do anything else of hers, odd as it sounds.
Of course, the power of those ‘90s classics is that they saw heavy recurrent play on my station during the time, so I can say I grew up with her music … just not in quite the traditional way. And, so long as I’m being honest, one reason I’ve delayed this feature for what seems like forever is that, when it came to Yearwood, I really only knew those huge hit singles. The albums tell a more fascinating story, from the powerhouse balladeer who debuted with a self-titled effort, only to transition into fiery blues-rock and grittier subject for Hearts in Armor. And it’s that back-and-forth transition between powerhouse balladeer and more fiery hellraiser that I think has characterized her work for the better, enough to where outside of maybe the slicker Where Your Road Leads and a disappointing comeback in Every Girl – or the occasional set that’s a bit too ballad-heavy – she’s been one of the most consistent artists to ever grace the format.
If anything, though, it made it harder to pick true standouts when there was such a consistent level of quality, so while I did go through every album of hers multiple times out of due diligence and to dig for those hidden gems, the truth of the matter is that many of her best songs hide in plain sight as radio singles – and damn excellent ones, to boot. With that said, here are my 15 favorite songs of hers; I invite you to share yours, too.
No. 15, “XXX’s & OOO’s (An American Girl)” (written by Matraca Berg and Alice Randall)
I could just leave it at, “It’s really catchy” (because it is), but back before the country music industry grew afraid of strong-minded women, artists like Yearwood, Mary Chapin Carpenter, and Pam Tillis recorded songs that were vital to that perspective during the decade. And while you can make comparisons of this to songs like, say, “He Thinks He’ll Keep Her” or “Shake the Sugar Tree,” this isn’t so much about breaking the struggle as it is her claiming her own agency within it, proving that she can “make it” just as well as her male counterpart can, all with God, wine, and Patsy Cline to keep her company. But, like, yeah, there’s also that fiddle lick and hook to add a vibrancy to that good fight. Oh, and it was the first No. 1 country hit penned by a Black woman – author Alice Randall, to be specific – so to all of you people who say artists need to write their own material because it’s pointless otherwise – shaddup.
No. 14, “I’m Still Alive (You’re Gone)” (written by Al Anderson and Matraca Berg)
I called Yearwood a hell-raiser in my introduction, but I don’t think that’s quite the right way to frame it. She’s not primarily known for kiss-offs; her way of getting back at old flames is just to project confidence and move on, which has always reflected a frank maturity in her work and her delivery that makes her best moments like these almost seembcathartic. And that works to this track’s benefit, where the groove is subtle and understated but still a potent slow burn, all the same, and there’s just enough rough edge in the guitar tones to give this firepower while maintaining its sense of normalcy. “Said I’ve love you till the day that I die … you’re gone and I’m still alive” is a damn cutting way to wrap it all up, too.
No. 13, “Hello, I’m Gone” (written by Kevin Welch)
Only Yearwood could make a song about escaping a bad, presumably abusive relationship sound like a cheery bar sing-a-long. Again, though, it’s that confidence and optimism that’s the key, where even despite breaking down on the road and having second thoughts about whether or not this character is cut out for the escape, she presses on, because while no one ever said the journey would be easy, it’s a hell of a lot better than going back to nothing.
No. 12, “This Is Me You’re Talking To” (written by Tommy Lee James and Karyn Rochelle)
Oh yeah, overproduction – another reason why people don’t look at the 2000s too fondly. That aside, this is the first piano ballad of many on this list that Yearwood just knocks out of the park, nailing the emotional vulnerability of a woman who hopes to reconnect with an old flame and doesn’t, because he’s moved on. Her delivery here is everything, because there’s a duality present here in the tone and framing she nails, where even though she knows she needs to move on and that it’s not her former partner’s fault that he fell out of love with her, she can still act hurt over the way that he’d try to make an awkward encounter in public anything more than it is. It’s just relatable in a way that can set back a process in motion and make all of those old demons resurface, and that flood of emotions is handled impeccably here … you know, on a technical level.
No. 11, “Lying to the Moon” (Matraca Berg and Ronnie Samoset)
Despite being recorded over a decade prior, this may as well be the spiritual successor to “This Is Me You’re Talking to,” another piano ballad Yearwood knocks out of the park, where her character reminisces on what will never be and every memory floods back as soon as that huge chorus hits. Beautiful imagery aside, I don’t have much to add other than that; sometimes the song speaks for itself, whether it’s being truthful or not.
No. 10, “Woman Walk the Line” (Emmylou Harris and Paul Kennerley)
I mean, Yearwood unearths an old Emmylou Harris song and gets her to add her fantastic counterbalance to it; it’s not that hard to make me happy. Still, considering I would say this track could stand alongside Yearwood’s own tracks and not feel out of place, it’s a testament to how trailblazers like Harris paved the way for a new generation of female voices and perspectives. Plus, I love songs where the backing vocals add a subtle touch to the subject matter at hand, as if Harris is here to support Yearwood drowning herself in misery, because she’s been there as well. Either way, it’s a fantastic song made even better.
No. 9, “Lonesome Dove” (written by Carl Jackson and Larry Cordle)
As the closing track to a terrific debut album, “Lonesome Dove” is just yet another fantastic heartache ballad Yearwood nails, sporting a cool blend of a waltz cadence with a restrained lyric you might expect out of bluegrass (especially seeing as how Larry Cordle helped pen this). And in relating the titular bird’s lonesomeness to her own, she accents every moment with pure excellence. “You’ve been forever forsaken by the one you love” – one of those moments you just feel and get.
No. 8, “Let the Wind Chase You” (feat. Keith Urban) (written by Sally Barris and Karyn Rochelle)
This one caught me off guard, a terrific duet with Keith Urban where he can actually match Yearwood in terms of intimate vulnerability on display, and where I just love the warm restraint exercised here in the tempered acoustics and strings. Like with “Lying to the Moon,” too, the imagery and metaphors used to capture the desperate hopelessness of wishing for a partner to try a bit harder is what really grounds this in further.
No. 7, “Where Are You Now” (written by Kim Richey and Mary Chapin Carpenter)
This is exactly the sort of opening track Yearwood needed after the more polished and tepid Where Your Road Leads, a Celtic-inspired roots-rocker that just builds to fantastic highs in its progression as our protagonist unleashes her frustrations with a distanced, flighty partner … that radio, apparently, didn’t care to hear. It’s direct and sensual in a way you’d expect from the writers, and with Yearwood carrying it, the message gets across.
No. 6, “Mr. Radio” (written by Roderick Taylor)
If you’re thinking that this song sounds a bit older in concept and delivery, it’s because it’s actually a Linda Ronstadt cover, and even the song’s theme here predates her own version, capturing rural America in the 1950s, when radio was the only way to connect with the outside world. It’s always been that mix of melancholic exhaustion and slight joy I’ve loved about this, where the days might be long and hard, but at the very least, there’s the joy of music to look forward to at its end. It’s the sort of story that’s literally defined what inspired early country music stars to go on to become legends, and it’s one worth passing on throughout time.
No. 5, “She’s In Love With the Boy” (written by Jon Ims)
It had to be here, but I’ll also say that, after going through the rest of her discography, this might seem like an anomaly for her – a relentlessly upbeat track augmented by a bouncy fiddle line that simply tries to play coy with any dramatic stakes it carries and little more. But if you’ve read this far in this feature, you know that every element of a great Yearwood track is here, right down to the measured storytelling and performance that she is in full control of, as well as the full independence for its characters to feel unique and in control of their own situations – that final verse is an all-timer. Oh, and it was Yearwood’s debut single, so there was really never any issue of her needing to come into her own as an artist. But even though she’d outdo herself on a few occasions afterward, this arguably remains one of her best. Sing along – you surely know how it goes.
No. 4, “Georgia Rain” (written by Ed Hill and Karyn Rochelle)
This is the 2000s version of “Strawberry Wine,” and I mean that as a huge compliment (as if the placement on this list didn’t speak for itself anyway). After all, this one stands on its own through its fiery passion and intensity displayed throughout that only Yearwood could have handled this effectively. This is a regretful yet sensual slow burn where the imagery is vivid enough on its own but made whole by its mature perspective looking at it all in hindsight. Again, it’s a familiar tale to revisit, but when said revisit includes magic like this, it’s always worth one more dance in the rain.
No. 3, “On A Bus to St. Cloud” (written by Gretchen Peters)
You may or may not recognize this one. It was a single … albeit one that completely floundered on the charts, and while I’d certainly understand why if it had been released a decade later, for 1995, audiences were robbed of a real stunner. I’ve always loved this one, but it wasn’t until I revisited it that its impact really hit me like it hadn’t before, a song that accentuates the torture an old friend’s memory has on someone – especially on that bridge. The thing is, it’s a song reflecting on a loved one’s suicide, which Yearwood didn’t know when she recorded it; that you can’t tell the difference and she gives it the proper weight it deserves … that kind of says it all, really.
No. 2, “The Song Remembers When” (written by Hugh Prestwood)
I thought for sure this would be my easy No. 1 pick before I started to work on this feature. The “song about songs” trend has made an odd comeback in recent years, but those checklist odes to nothing pale in comparison to this song that uses music as a painful way to revisit a past relationship … but also indulge in the memory, because sometimes remembering the good parts can help it rise to a bittersweet level, at least. Kris Kristofferson himself has called Yearwood the finest interpreter of song, and for how excellent of a vocalist she is, it’s worth deconstructing that claim. Despite the fact that she easily could, she never belts; she always stays within the emotional boundaries that a song benefits from and, in essence, requires to even work. Here, she moves from the pure shock of how these memories she thought she had forgotten come back to her, only to let them completely crush her by the end – a tricky emotional balance that she perfects. It’s the kind of song everyone likely relates to in some form, and it’s one of the finest songs of the ‘90s.
As always, before I get to my No. 1 pick, here are a few honorable mentions that just barely missed the cut for my list, ranked in no particular order:
“When Goodbye Was a Word” (written by Gene Nelson and Paul Nelson)
“Heaven, Heartache & the Power of Love” (written by Clay Mills and Tia Sillers)
“The Woman Before Me” (written by Jude Johnstone)
“Wrong Side of Memphis” (written by Gary Harrison and Matraca Berg)
“For Reasons I’ve Forgotten” (written by Jamie O’ Hara)
“Victim of the Game” (written by Garth Brooks and Mark D. Sanders)
“Under the Rainbow” (written by Matraca Berg and Randy Scruggs)
And now, my No. 1 pick:
No. 1, “Dreaming Fields” (written by Matraca Berg and Gary Harrison)
I hadn’t revisited this one in probably over a decade, and while it had always been a favorite of mine, I think the weight of time and experience of loss is what made it hit harder than ever before for me. There are certainly bad ways to exercise nostalgia. At its worst, it can be weaponized or used to conjure images of “good ol’ days” that weren’t actually that great. And, if we’re being honest, we don’t miss actual pastimes; we miss the way we felt during them: younger, more innocent, and able to see the world with wonder in a way that’s harder – no, damn near impossible – to replicate as adults. I spent the bulk of the pandemic cleaning out my grandparents’ house after their respective deaths, and I can’t accurately describe that simultaneous feeling of happy nostalgia I felt from revisiting rooms I saw myself in as a child and sadness I felt knowing I was looking at it from a colder, empty present day, and that soon I wouldn’t be able to return to them again … that is, in a physical sense.
So when I say I get what both Yearwood and writers Matraca Berg and Gary Harrison were going for here – capturing bygone days with a childlike attention to details that might pass us by, like corn waving in the breeze, rain on a rusted plow, or even a regular scarecrow, all with the realization that they won’t return and that the images captured now are of a worn-down landscape lost to time – I get it. It’s also more than that, however. It captures the hardships that have come in the modern day for farmers and a way of life that can be difficult and unsustainable. But it’s that basic emotional core that resonates even louder now than ever before, and while its legacy is simply cemented as a fantastic deep cut, it’s a song worth harvesting, even if the memories it dredges up are bittersweet.