When it comes to country love songs, the ’90s had an embarrassment of riches, and whittling this list down to 16 entries took more than a few tough judgment calls.
How, for example, do you weigh the merits of something like Tim McGraw and Faith Hill’s “It’s Your Love” against a song as brilliant as Hill’s “This Kiss”? How do you decide if “Maybe It Was Memphis” by Pam Tillis or “Cowboy Take Me Away” by The Chicks is the best song? What makes one love song better than another?
These are tough questions, and we don’t have the answers. What we have is this hand-picked list of the best love songs from country music’s greatest decade that we feel is definitive.
Here we are.
15. “Meet in the Middle”, Diamond Rio
We could all learn a little from Diamond Rio. The band’s signature song and defining hit of the decade, “Meet in the Middle” is an ode to the one constant in every romance. Compromise.
14. “Carry Your Love With Me”, George Strait
If only long-distance love were as easy as George Strait makes it sound on a 1997 song, in which he plays the role of the traveling (but also extremely loyal) cowboy. Swoon.
13. “Just in Time”, Lucinda Williams
The opening of the desire to Car wheels on a gravel roadLucinda Williams’ 1998 masterpiece, makes evocative poetry of its narrator’s worldly desires.
12. “If I could make a living”, Clay Walker
We feel that “lovin'” has a double meaning on this essential Clay Walker bop from 1994. More power for him.
11. “Don’t Let Our Love Start To Slip”, Vince Gill
Not a love song in the traditional sense, “Don’t Let Our Love Start Slippin’ Away” nonetheless features some of Vince Gill’s most passionate vocal work. Turns out the Eagles are big fan as well.
10. “Two Sparrows in a Hurricane”, Tanya Tucker
“The world says they’ll never make it / Love says they will,” Tanya Tucker sings in this sweeping and tender story song about a pair of teenage lovers who defy the odds and stay together into old age. It narrowly missed out on the number one spot on radio, but remains one of the defining songs of her mid-career resurgence period. (See also: Alan Jackson’s “Livin’ On Love” from 1994.)
9. “You’re still the only one”, Shania Twain
No karaoke bar was ever the same after Shania Twain released “You’re Still the One,” the platonic ideal of the crossover single, in early 1998. The fact that it never peaked from Billboard Hot 100 simply defies belief.
8. “Strawberry Wine”, Deana Carter
Never, and I mean never, has the loss of her virginity sounded so tender and beautiful as in “Strawberry Wine.” The first of Carter’s three early No. 1s, Did I shave my legs for this?, “Strawberry Wine” remains in many ways the standard by which country daydreams are measured.
7. “She’s in love with the boy”, Trisha Yearwood
30 years after the release of “She’s in Love with the Boy” — simply put, a picture-perfect song — Yearwood made country music history by singing “She’s in love with the daughter“, on stage at the Grand Ole Opry Opry with rising star Brooke Eden in honor of Pride and Eden’s engagement to his fiancée Hilary Hoover. Love indeed wins!
6. “When You Say Nothing At All”, Alison Krauss & Union Station
Recorded for the years 1995 Keith Whitley: A Tribute Album, Alison Krauss and Union Station’s version of “When You Say Nothing At All” reinterprets Whitley’s beloved original and reinterprets it as a pop-rock jam. Even as love songs, it doesn’t get much smoother than that.
5. “Until a Tear Becomes a Rose”, Keith Whitley with Lorrie Morgan
After Whitley’s tragic death in 1989, Lorrie Morgan added her own vocals to her demo version of Leon Everette’s “Til’ a Tear Becomes a Rose” creating one of the most heartbreaking love songs ever. country’s history.
4. “Maybe it was Memphis”, Pam Tillis
Dissertations could be written (and perhaps already have been?) on the second verse of this towering Southern romance, which draws a sharp line from William Faulkner and Tennessee Williams to Glen Campbell and straight to ’90s country. A masterpiece.
3. “Cowboy Take Me Away”, The Chicks
It would be impossible to overstate the importance of this song to any queer person growing up in the late 90s or early 2000s. God bless the chicks.
2. “That Kiss”, Faith Hill
The second half of the decade spawned many crossover hits, a few of which were even bigger than Hill’s “This Kiss.” None, however, can claim to have made rhyme “centrifugal movement” with “pivotal moment”. No one can ever take that away from him.
1. “In spite of us”, John Prine and Iris DeMent
The brilliance of “In Spite of Ourselves,” the title track from John Prine’s iconic 1999 duet album, is that it doesn’t glorify its subjects. Far too many love songs (including, uh, a few entries on this list) lean so far into the romance of it all that they lose sight of what makes love so remarkable: anyone, even the two strange narrators of this classic song, can find their “grand door prize”. I want to say that.
READ MORE: Let’s Go Girls: 40 Women Who Shaped 90s Country