Key Western Fest 2024 Showcases Landmark Era for Country Women

At the inaugural Key Western Fest in Key West, Florida in 2023, a recurring narrative in conversations was how the women of ’90s country had held up so much better than the men. There were exceptions to that rule of course. Clint Black most certainly still had it, and Neal McCoy remains one of the hottest firecracker performers in country.

But a festival that was founded to cater to the resurgent interest in ’90s country picked up on something important: the ’90s weren’t just the last time popular country sounded country, it was also the last time when country women played a major role in mainstream country while showcasing a diverse variety of styles and influences. From traditionalists, to more folk and rock-oriented performers, to country pop with great songwriting, it all has withstood the test of time.

It wasn’t the original intent by the promoters of Key Western Fest to host a festival in 2024 where women made up all the main headliners and primary performers. It just happened to be that’s how it worked out as they started putting their lineup together and realizing what a treasure trove of talent the women of ’90s country are. Add a few new women who are inspired by the ’90s country greats, and Key Western Fest assembled one of the most talent rich lineups country music will see all year.

When Deana Carter took the stage for the kickoff party Tuesday evening on Key West’s iconic Sunset Pier, the weather had turned brisk after being hot for most of Key Western’s sister fest, the Texas/Red Dirt-oriented Mile 0 Fest. But nobody cared, Carter and her kickass band warmed up the crowd quickly, and everyone will remember singing “Strawberry Wine” under the stars in Key West on a pier extending out into the ocean.

Deana Carter
Key West’s Sunset Pier at night

Carolyn Dawn Johnson and Jamie O’ Neal were relative outsiders in country at the start of their careers since they came from Canada and Australia respectively. But both persevered to mint major hits in the early ’00s. Both also still put on stellar shows, and when Jamie O’ Neal took the stage Saturday to open the fest, Carolyn Dawn Johnson who’d opened on Thursday came out to sing backup for O’Neal. This kind of camaraderie among the performers persisted throughout the week.

On Saturday, Pam Tillis and Lorrie Morgan played back to back. Pam Tillis made her Grand Ole Opry debut at the age of 8 with her father Mel Tillis. Lorrie Morgan made her Grand Ole Opry debut at the age of 13 with her father George Morgan. They both grew up backstage at the Opry, they both grew up together, and here years later, they’re still singing together, and are sitting on Hall of Fame-worthy careers.

Near the end of Lorrie Morgan’s set, Pam came out to reprise their “Grits and Glamor” duo project, singing “I Am a Woman” together.

Pam Tillis and Lorrie Morgan

Another strong narrative that came out of Key Western Fest was persevering through adversity. Both Tanya Tucker who headlined Wednesday, and Wynonna Judd who headlined Thursday have seen the best and worst of the country music business and fame. They also both survived it to be recently named Country Music Hall of Famers.

On cue, Tanya Tucker came out on stage and kicked ass with “Outlaw” emblazoned on the back of her jacket, even though she was disobeying doctor’s orders after recent neck surgery. “I should be home in bed, but the hell with that!” she said strutting and posing per usual. She sang all the hits, but was extra talkative, telling the story of her life in country music that’s gone from child prodigy, to a mainstream star, to an Outlaw survivor, ultimately minting major hits in three decades.

After the show, there was major stir outside the amphitheater as people were filing out. It turned out that Tanya had stopped to mingle and take photos with fans. The police rushed over, and soon they were taking photos with Tanya, and snapping photos for others too. Tucker’s bus was supposed to leave the next morning, but sat in Key West for days. Apparently Tucker overdid Key West, which is an easy thing to do.

Tanya Tucker, Outlaw

It wasn’t a “performance” from Wynonna on Thursday night, it was church. The power emanating from this woman is unparalleled. For many, Wynonna turned in the crown jewel performance of Key Western Fest. Her humility and graciousness with the crowd is something attendees talked about all week, and her encore performance of “Mama He’s Crazy” with just an acoustic guitar is something the audience will never forget.

After Wynonna’s phenomenal performance on Thursday, you had to wonder how Lee Ann Womack would rise to the occasion on Friday. She did it by being just as stellar, but in a completely different manner. It may have seemed a little redundant when Lee Ann Womack walked out on stage at Key Western Fest Friday night and said, “We’re gonna play some COUNTRY music,” but it was the perfect way to describe what was about to transpire.

Womack promptly started singing some of the saddest, slowest, and most gorgeous country music you’ve ever heard in your life. She even had the band join her around one microphone to sing songs like “Wayfaring Stranger” and “Long Black Veil.” It was a clinic on true traditional country music, and one that found incredible favor with the crowd.

Of course Womack also sang what she referred to as her “older stuff” like “I Hope You Dance,” and it was incredible as well. Lee Ann Womack is the embodiment of true class in country, and a landmark singer who should be joining her other Key Western Fest headliners in the Hall of Fame sooner than later.

Lee Ann Womack

Elizabeth Cook as a performer sits between the eras of women in country. Once banned from country radio for releasing a song with “balls” in it, just like so many of the women on the lineup, she’s a survivor. Perhaps these days, Cook is just as well known as a DJ on Sirius/XM, but she remains a hell of a performer with a fun show.

Terri Clark has also worked as a radio personality in her career. But as she proved at Key Western Fest, the stage is where she belongs. Women who are both songwriters and performers was also one of the highlights of the festival. Suzy Bogguss made a return appearance to the festival after being one of the highlights in 2023, and even took the stage at one point during Terri Clark’s set to satisfy the urge for more cowbell.

Terri Clark
Suzy Boggus on the cowbell

Sarah Evans also returned from 2023, and aside from her song “Suds in the Bucket,” she again struggled to fit with the overall vibe of the festival, not just on the stage (where she disallowed photographers to get close), but some members of security said she was the sole diva-acting performer over the weekend. As always though, she turned in a great set of what Sarah Evans does.

And you can’t have a proper festival without up-and-comers and moments of discovery. Brit Taylor from Kentucky performed on Wednesday ahead of the release of her new bluegrass album Kentucky Bluegrassed. Lillie Mae and Nikki Lane both opened the show on Friday, and showcased how the women of independent country are holding onto the traditions set by country women, while making a few new ones of their own.

Lillie Mae

Mickey Guyton was one of the wild cards on the lineup as the one artist with current mainstream country relevancy, as well as a more contemporary pop country sound. It wasn’t an easy position for Guyton to be put in, and though you always hope for mainstream stars on independent/classic country lineups to cater their sets to the audience, they rarely do.

Guyton did play “Blame It On Your Heart” by Patty Loveless, which got a huge rise from the crowd. Then the next song featured drum machine beats controlled by the laptop in front of the bass player. When Guyton introduced a song as being co-written with Tyler Hubbard of Florida Georgia Line, it was confirmation that she didn’t really know where she was.

But by the end of the show, Guyton had endeared herself to the audience by talking about how becoming a mother inspired her song “Scary Love,” and how her husband’s illness had inspired another song. Guyton was also energetic and entertaining, and nobody has ever questioned her singing ability. By the conclusion of her performance, the crowd gave her strong applause, and she definitely had made some new fans.

Mickey Guyton

And even though it was a woman-oriented lineup, there were a few male performers who participated, namely Jim Lauderdale who acted as emcee for a few days, and also performed during a day showcase before hopping on the Outlaw Country Cruise with Nikki Lane and Elizabeth Cook.

Key West-based songwriter Cliff Cody helped entertain at day parties, and an overlapping residency at Key West’s open-air Smokin’ Tuna bar featuring Matt Castillo made for some killer afterparties. Castillo continues to be one of the greatest traditionalists of our time who is criminally overlooked in the industry. He sounds like George Strait, moves like Dwight Yoakam, and is one hell of a good time.

Matt Castillo

Even though it was a (mostly) all woman festival, Key Western Fest was not a gripe fest at all. This wasn’t country music’s version of a Lilith Fair. Sure, some of the women weren’t shy talking about the lack of representation for women on country radio these days, and they shouldn’t be. But it was mostly about celebrating the artist and the era that women were on the radio, and emphasizing how this music still has merit and relevancy today, including to male listeners, who still made up a significant portion of the audience.

About the only gripe about Key Western Fest was the size of the audience overall. Though by the time the headliners took the stage each night, the Truman Waterfront Amphitheater felt full of love for good country music, it felt relatively empty for the opening acts. With a curious lack of media support for a lineup much of the media had been requesting and demanding for years, attendance numbers were far down from Key Western Fest’s inaugural year in 2023. This is an entirely other issue that will be dealt with in a dedicated manner in due course.

But for the people that were there and the performers that participated, Key Western Fest 2024 was a landmark success showcasing how the women of country’s past, present, and future deserve equal adulation, along with equal representation and support. An all-woman lineup may not happen again, but everyone will be talking for years about the time it happened at Key Western Fest 2024.

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All photos by Kyle “Trigger” Coroneos. Apologies to festival participants not mentioned or photographed. For more media from Key Western Fest check out Saving Country Music on Instagram.

Jo Dee Messina closed out Key Western Fest playing Journey’s “Don’t Stop Believing.”
Multi Grammy-winning and CMA Song of the Year winner Liz Rose was around all week, giving legitimacy to Key Western Fest and repping the most inappropriate Uncle Bekah’s Inappropriate Trucker Hats.
More Wynonna
Wynonna drummer and husband Cactus Moser
Pam Tillis
Fiddle player and singer Ivy Phillips plays a big role in the band of Pam Tillis
Haley Sullivan is a great singer as well, and the music director for Pam Tillis
Nikki Lane
Mickey Guyton
Lorrie Morgan on the amphitheater stage
Lorrie Morgan officially won the “Cool shoes contest” over the weekend.
Terri Clark and band
Tanya’s band all were sporting jumpsuits, similar to Mike Harmeier of Silverada
Elizabeth Cook
Elizabeth Cook guitar player Andrew Leahey
Kylie Frey stayed over from the previous week’s Mile 0 Fest to open the launch party Tuesday night on the Sunset Pier
Jamie Lin Wilson emceed and performed at the San Carlos Theatre
Robert’s Western World in Nashville was a Key Western Fest sponsor, and served up recession specials of fried bologna sandwiches, a bag of chips, and a Moon Pie.
Jim Lauderdale came out to perform with Lillie Mae
Lillie Mae’s sister and mandolin player Scarlet Rische
Brit Taylor
Jamie O’Neal definitely knows how to bedazzle her mic stand.
Lee Ann Womack and band performing traditional country standards around one mic.
Jim Lauderdale
Erica Sunshine Lee playing a day party at The Smokin’ Tuna
Cliff Cody at Hank’s Hair of the Dog
Key Western Fest/Mile 0 Fest head honcho Kyle Carter
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