Trisha Yearwood's best-known songs from the '90s point back to a time when talented women got a fair shake in Nashville, allowing a wide range of listeners to discover not just the Georgia native but many of her talented peers.
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Yet focusing on those halcyon days of country music tells just one part of the story. One of the best singers in the game —and one of the most glaring omissions from the Country Music Hall of Fame (though her day will surely come)— remained relevant past those early years. She's always delivered when it comes to new music. For example, she delivered most recently in 2019 with two albums: the Frank Sinatra tribute disc Let's Be Frank as well as Every Girl. The latter sounded like a vital addition to playlists at the time as opposed to an audio victory lap by a legacy artist.
Through her sustained greatness, Yearwood has become a celebrity chef and TV personality, positioning her to inspire new fans to look up her musical past.
Whether solo or with Garth Brooks as her duet partner, Yearwood's been among Nashville's most elite and most beloved talents for over 30 years.
Here's our playlist of the 12 greatest hits by a Grand Ole Opry member and multi-time CMA, ACM and Grammy award winner.
Jason Kempin/Getty Images for Country Music Hall of Fame and Museum Yearwood has stayed traditionally country by changing with the times. That's to say that just as she fit right in on country radio in the '90s along with Alan Jackson and other traditionalists, she's proven to be just as worthy a match of Chris Stapleton and other "old souls." Rick Diamond/WireImage for The Recording Academy Yearwood's the type of singer who can elevate even the most gifted vocalists. Here, her smooth delivery magnifies the deep, baritone delivery —and heartfelt storytelling approach— of Josh Turner. John Shearer/Getty Images for the Country Music Association In recent years, Yearwood has taken her fellow Georgia native Lauren Alaina under her wing. As a result of this mentorship turned friendship, Yearwood guested on one of the better songs off Alaina's breakthrough 2021 album. Dominik Bindl/Getty Images Real recognized real when Yearwood covered a song co-written and first cut by Ashley McBryde. As if that wasn't enough of an honor for McBryde, Yearwood recruited Kentucky country legend and future Country Music Hall of Famer Patty Loveless as her duet partner. Pete Mitchell/WireImage When Yearwood sings more sentimental songs that tell relatable stories, she's following in the bootsteps of Reba McEntire. Yearwood likely wouldn't deny this and would surely take being in the McEntire lineage of balladeers as a complement. Here, two legends that never lost a step joined voices. Bill Tompkins/Getty Images Beyond having a great voice, Yearwood's got that magical knack for making us feel the emotions in each song's lyrics. Here, she makes us feel all the breakup regrets in what sounds like a cross between an Aerosmith power ballad and an '80s country flashback. Bill Steber/Getty Images Yearwood entered the new century as she left the prior one: with songs grounded in country tradition yet epic enough to soundtrack any major motion picture. Take for instance this love song about having no regrets at all which could've spun off its own rom-com. Bonus points for surprise displays of rock 'n' roll guitar heroics. Paul Morigi/Getty Images Although the '90s gets rightfully celebrated as a time when line-danceable honky-tonk tunes ruled the airwaves, it was also one of the golden ages for slowed-down material. Yearwood's among the best as singing such material. Note that this Kris Kristofferson-inspired song is a co-write by Brooks, meaning that the two have been elevating each others' talents for over 30 years. SGranitz/WireImage The narrator in the second single from Everybody Knows admits they were playing it cool when acting like they weren't giddy about a potential relationship with whoever's on the other end of the phone. The admission of "wounded pride" became the fourth of five Yearwood singles to top the Billboard Hot Country Songs chart. Tim Mosenfelder/Getty Images Yearwood sings of wistful daydreaming about a special someone on what became the third No. 1. She sounds great, as usual, so there's something else setting this one apart: slide guitar accompaniment by fellow country star Lee Roy Parnell. David Redfern/Redferns A rundown of the best Yearwood songs would be incomplete without this one, even if LeAnn Rimes' stellar rendition of a Diane Warren original might be better-known now. This recording that made it in the film Con Air and earned Yearwood a Grammy Award will always represent a particular moment in pop culture history. M. Caulfield/WireImage for Bragman Nyman Cafarelli The main selling point of Yearwood's 2005 comeback album Jasper County remains this sentimental song that references the singer's home state. It's a five minute-plus story-song that's a near-perfect showcase of Yearwood's mighty alto vocals. William Campbell/Sygma via Getty Images Like Sara Evans and other country singer peers, Yearwood came out the gate with traditional-sounding country songs. Take for instance this 1991 cut that's a honky-tonk throwback. Indeed, the co-write by underrated solo artist Kevin Welch is as rollicking as anything by Alan Jackson or anyone else in Nashville. Ron Galella, Ltd./Ron Galella Collection via Getty Images This Yearwood and Brooks duet is good enough to warrant consideration for his and her best songs lists. It left enough of an imprint on country music that it would've linked them together forever without their future marriage. Other duets of note range from Yearwood's second single ever, 1991's "Like We Never Had a Broken Heart," to the title track of Yearwood's 1998 studio album Where Your Road Leads. Ron Galella/Ron Galella Collection via Getty Images Yearwood's offering that best mirrored some of her peers' bluesy, rocking vibe also features classic country instrumentation, accentuating a story-song with a strong sense of place. This was the first single on her second album, Hearts in Armor. Ron Galella/Ron Galella Collection via Getty Images One of the saddest songs of its time, "Walkaway Joe" teams Yearwood with the Eagles' Don Henley for a tale of hard living and broken hearts. Bonus points for a music video that stars a then-unknown Matthew McConaughey. Ron Galella, Ltd./Ron Galella Collection via Getty Images This weepy ballad remains one of the best examples of Yearwood's vast talent as a soulful vocalist and emotive song interpreter. The song was written by Hugh Prestwood and originally recorded by Kathy Mattea, though it never made it onto one of her albums. David Redfern/Redferns High-energy '90s country, custom made to match the scope of a stadium show, suited Yearwood's mighty voice, as heard on this classic single about what a powerful thing love is and what a joy it is find it. It's one of several bonus tracks from a greatest hits compilation that made it onto our list. Ron Galella/Ron Galella Collection via Getty Images Often, a great country song's narrator tells a first-person story that's relatable to people from all walks of life. Yearwood really does sing for the small-town, all-American youngster on this co-write by the great Alice Randall and Matraca Berg. It's the lead single from platinum disc Thinkin' About You. Ron Galella/Ron Galella Collection via Getty Images As usual, it's hard to argue against the most obvious song being an artist's best. Yearwood's debut single still gets stuck in the heads of anyone who runs across it on a streaming playing— or, in true '90s fashion, gives her self-titled debut album a spin."Workin' on Whiskey" (Every Girl, 2019)
"Another Try" (With Josh Turner) (Turner's Everything is Fine, 2007)
"Getting Good" (With Lauren Alaina) (Alaina's Setting Pretty on Top of the World, 2021)
"Bible and a .44" (With Patty Loveless) (Every Girl, 2019)
"She Can't Save Him" (With Reba McEntire) (McEntire's Reba Duets, 2007)
"There Goes My Baby" (Where Your Road Leads, 1998)
"I Would've Loved You Anyway" (Inside Out, 2001)
"Like We Never Had a Broken Heart" (Trisha Yearwood, 1991)
"Believe Me Baby (I Lied)" (Everybody Knows, 1996)
"Thinkin' About You," (Thinkin' About You, 1995)
"How Do I Live" ((Songbook) A Collection of Hits, 1997)
"Georgia Rain" (Jasper County, 2005)
"That's What I Like About You" (Trisha Yearwood, 1991)
"In Another's Eyes" (Feat. Garth Brooks ((Songbook) A Collection of Hits, 1997)
"Wrong Side of Memphis" (Hearts in Armor, 1992)
"Walkaway Joe" (With Don Henley) (Hearts in Armor, 1992)
"The Song Remembers When" (The Song Remembers When, 1993)
"A Perfect Love" ((Songbook) A Collection of Hits, 1997)
"XXX's and OOO's (An American Girl)" (Thinkin' About You, 1995)
"She's In Love With The Boy" (Trisha Yearwood, 1991)
This story was first published in 2018. It was updated and expanded on March 5, 2024.
