15 Love Songs Representing the Heart of '90s Country

As country love songs go, the '90s had an embarrassment of riches, and narrowing this list down to 16 entries required more than a few tough judgment calls.

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How, for instance, does one weigh the merits of something like Tim McGraw and Faith Hill's "It's Your Love" against a song as plainly brilliant as Hill's own "This Kiss"? How does one decide whether "Maybe It Was Memphis" by Pam Tillis or "Cowboy Take Me Away" by The Chicks is the better song? What makes one love song better than another, aside from the day of the week and the listener's personal situation?

These are tough questions, and we don't have the answers. What we do have is this hand-picked list of the best love songs from country music's greatest decade, which we feel is definitive.

Here we go.

 15. "Meet in the Middle," Diamond Rio (Diamond Rio, 1991)

We could all learn a little from Diamond Rio. The group's signature song and a defining hit of the decade, "Meet in the Middle" is an ode to the only constant in every love story: compromise. It became the first debut single by a country band to reach No. 1. Listen here.

14. "Carrying Your Love with Me," George Strait (Carrying Your Love With Me, 1997)

If only long-distance love was as easy as Strait makes it sound on song from 1997, in which he plays the part of the roving (but also extremely loyal) cowboy. Of course, it'd be hard to narrow down a list of 15 if we were only working with King George's back catalog. Listen here.

13. "Right in Time," Lucinda Williams (Car Wheels on a Gravel Road, 1998)

The yearning opener from Car Wheels on a Gravel Road, Lucinda Williams' 1998 masterpiece, makes evocative poetry of its narrator's mundane desires. It's a top-shelf song by a top-shelf singer-songwriter. Listen here.

12. "If I Could Make a Living," Clay Walker (If I Could Make a Living, 1994)

One gets the feeling that "lovin'" has a double meaning on this essential bop and heavy-hitting fiddle tune from 1994. It's one of several romantic selections from one of the decade's best cowboy Casanovas. Listen here.

11. "Don't Let Our Love Start Slippin' Away," Vince Gill (I Still Believe in You, 1992)

Not a love song in the traditional sense, "Don't Let Our Love Start Slippin' Away" nonetheless features some of Gill's most impassioned vocal work-- which is saying something when considering his deep, multi Grammy award-winning catalog. Listen here.

10. "Two Sparrows in a Hurricane," Tanya Tucker (Can't Run From Yourself, 1992)

"The world says they'll never make it / Love says they will," 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 just missed the No. 1 spot at radio, but remains one of defining songs of her mid-career resurgence, period. Listen here.

9. "You're Still the One," Shania Twain (Come on Over, 1997)

No karaoke bar was ever the same after Twain released "You're Still the One," the platonic ideal of the crossover single, in early 1998. The fact that it never reached the top of the Billboard Hot 100 simply defies belief. Listen here.

8. "Strawberry Wine," Deana Carter (Did I Shave My Legs For This?, 1996)

Never, and I mean never, has the loss of one's virginity sounded as tender and beautiful as it does on "Strawberry Wine." The first of three No. 1 from Carter's debut album, "Strawberry Wine" remains in many ways the standard by which country reveries are measured. Listen here.

7. "She's in Love with the Boy," Trisha Yearwood (Trisha Yearwood, 1991)

Thirty years after the release of "She's in Love with the Boy" — simply put, a perfect song — Yearwood enshrined her signature hit into country music history by singing "She's in love with the girl," onstage at the Grand Ole Opry with rising star Brooke Eden in honor of Pride and Eden's engagement to fiancée Hilary Hoover. Listen to the original here.

6. "When You Say Nothing at All," Alison Krauss & Union Station (Keith Whitley: A Tribute Album, 1995)

Recorded for 1995's Keith Whitley: A Tribute Album, Krauss and Union Station's version of "When You Say Nothing At All" reinterprets Whitley's beloved original as a pop-rock jam. Even as love songs go, it doesn't get much smoother than this. Listen to Krauss' version here.

5. "Til' a Tear Becomes a Rose," Keith Whitley with Lorrie Morgan (Whitley's Greatest Hits, 1990)

After Whitley's tragic death in 1989, a bereft Morgan added her own vocals to his demo version of Leon Everette's "Til' a Tear Becomes a Rose," in the process creating one of the most heart-rending love songs in country music history. Listen here.

4. "Maybe It Was Memphis," Pam Tillis (Put Yourself in My Place, 1991)

Dissertations could be written (and maybe already have been?) about the second verse of this towering Southern romance, which draws a clean line from William Faulkner and Tennessee Williams through Glen Campbell and straight to '90s country. It was written in 1983 by Michael Anderson and previously recorded by powerpop legend Phil Seymour. Listen to Tillis' version here.

3. "Cowboy Take Me Away," The Chicks (Fly, 1999)

It would be impossible to overstate the importance of this song to any queer person who grew up in the late '90s or early aughts. God bless the Chicks for this and other selections from a deep and well-aged catalog. Listen here.

2. "This Kiss," Faith Hill (Faith, 1998)

The latter half of the decade spawned numerous crossover hits, a few of which were even bigger smashes than Hill's "This Kiss." None, however, can boast that they rhymed "centrifugal motion" with "pivotal moment." No one will ever be able to take that away from her. But seriously, this is a decade-defining love song. Listen here.

1. "In Spite of Ourselves," John Prine and Iris DeMent (In Spite of Ourselves, 1999)

The brilliance of "In Spite of Ourselves," the title track from Prine's iconic 1999 duets album, is that it does not glorify its subjects. Far too many love songs (including, ahem, 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 "big door prize" with a significant other. Listen here.

This story previously ran on May 26, 2022.

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