10 of Garth Brooks’ Greatest Hits — And the Stories Behind Them — Of All Time

Two months from now, Garth Brooks will embark on his Las Vegas Residency, Garth Brooks/Plus ONE, at Caesars Palace. Beginning on May 18 and lasting until 2024, fans are promised a “once-in-a-lifetime performance each and every night,” according to the venue’s website.

But before all the awards and accolades and sold-out arenas, Brooks was just a humble performer telling stories through his songs. In the late 80s, he launched his stuff-of-legends career at Nashville’s renowned Bluebird Cafe, an intimate music venue wherein guests sit eye-level with — and very close to — musicians and songwriters, and get to listen in on the behind-the-scenes tales of how their favorite songs came to life. Brooks even returns to the Bluebird Cafe periodically, as he did on January 8, when he surprised attendees with an unannounced appearance. The venue is a must for any true country music lover. To prepare you for your visit (and, fingers crossed, spontaneous Garth Brooks’ performance) here are the stories behind 10 of his most enduring songs.

1. “Much Too Young (To Feel This Damn Old)” (1989)

One of the songs that Garth Brooks brought with him to Nashville in 1987, “Much Too Young (To Feel This Damn Old)” was originally supposed to be about a road-weary musician. “That’s pretty good,” his friend Randy Taylor told him. “But it could be better.” Taylor suggested that what it needed was a cowboy. So Garth flipped the script and opted to use one of his heroes, ex-rodeo champion Chris LeDoux, as the inspiration for the main character.

It was a stroke of genius. As the first single Garth released, it established him as a country singer with a very unique sort of authenticity, one that evoked the Great Plains and America’s heartland. LeDoux got name-checked directly in the song, a fact that Garth claimed helped give himself some credibility, but it proved mutually beneficial. With Garth’s help, LeDoux signed his own Capitol Records contract. The two later collaborated on 1992’s “Whatcha Gonna Do With a Cowboy.”

2. “If Tomorrow Never Comes” (1989)

Another cut that Garth had come up with before he left Oklahoma for Music City, this one didn’t come to life on the page until he met Kent Blazy, a Nashville songwriter. Garth had tried shopping the idea around to several other songwriters in Nashville, none of whom took an interest in it. But when he had his first meeting with soon-to-be-manager Bob Doyle, Doyle introduced him to Blazy.

“He had the first verse down within 15 seconds. I could tell he just felt it,” Garth recalled in the liner notes to The Hits, a 1994 compilation album. Though the finished product grew into a rumination on a father imagining what life would be like for his daughter once he’s gone, the roots of “If Tomorrow Never Comes” laid in the real-life deaths of two of Garth’s close friends from college, Jim Kelly and Heidi Miller — a onetime roommate of Garth’s — who died in a plane crash and car accident, respectively, in the mid-’80s. As his first love song and slow ballad and his first No. 1, it would hold a pivotal place in his musical development.

3. “The Dance” (1989)

Picking out one singular song as Garth’s defining hit is a near impossible task. However, “The Dance” would probably be your best bet. The singer has even said so himself, telling Playboy in 1994, “I’ll go to my grave with ‘The Dance.’ It’ll probably always be my favorite song.” Ironically, it took some convincing to get him to include it on his self-titled debut. Here, it appeared as the closing track and would ultimately serve as the final single.

Songwriter Tony Arata penned the song. He later wrote Clay Walker’s 1994 No. 1 “Dreaming With My Eyes Open” and Garth’s “The Change,” which reached the top two years after that. Still, when the time came, Garth and producer Allen Reynolds insisted it would be a perfect single. Its overwhelming success set him up for the one-two punch of “Friends in Low Places.” It also earned him his first Song of the Year award from the Academy of Country Music in 1990.

4. “Friends in Low Places” (1990)

Garth’s debut album did its job in establishing the up-and-comer as a singer and songwriter of great emotional depth and nuance. However, with the heft of “The Dance” helping put him over the edge, he needed to show fans his fun, carefree side. “Friends in Low Places” did that, and then some. It’s hard to imagine his catalog, much less one of his live shows, without this woozy, infectious sing-along. It actually got its title from a dinner that co-writer Earl Bud Lee had with a friend.

“Don’t worry,” the pal said when they got the check. “I have friends in low places. I know the cook.” It’s not surprising that its runaway success actually started as a word-of-mouth campaign. Radio disc jockeys latched onto the track before it had even been released as a single; this was thanks to Garth’s mother, Colleen, accidentally leaking it. Soon, listeners were calling into stations demanding to hear it played.

5. “The Thunder Rolls” (1990)

Though inextricably linked with the music video that stirred up so much controversy for its depiction of domestic violence, “The Thunder Rolls” was yet another of Garth’s original compositions from his early days in Nashville. It was initially given to another artist — in this case, no less than outlaw bad girl Tanya Tucker, who recorded it in 1988 for that year’s Strong Enough to Bend.

Tucker, uniquely, asked for an additional verse to be added. Garth and his co-writer, Pat Alger, duly accommodated her request. Yet Tucker ultimately decided against including the song on her album, which came as a relief to Reynolds. “That’s one of the most powerful songs I’ve ever heard!” he insisted. So Garth cut the song himself, minus the extra verse, for No Fences, with Alger joining in on acoustic guitar. After being released as a single in April 1991, the song became Garth’s fifth straight country No. 1.

6. “The River” (1991)

Besides being a world-class entertainer and all-around good guy, Garth is also a tireless cheerleader for his legions of fans, hoping they pursue their dreams and live their best lives. Never was that clearer than on “The River,” the standout track from his sensationally successful third album, Ropin’ the Wind. Ever intent on finding new imagery in his writing and inventive ways to articulate some of the world’s biggest ideas, the song uses its namesake as a metaphor for the creative process and the pursuit of one’s dreams.

“I live by this song every day and hope it gives courage to people who have ever been in a fight they didn’t know they could finish,” Garth said. He co-wrote it with one of his favorite writing partners, singer-songwriter Victoria Shaw, with whom he later penned the No. 1 “She’s Every Woman.” Trisha Yearwood also covered Shaw’s “Where Your Road Leads” in 1998, with Garth providing backing vocals.

7. “Ain’t Going Down (Til the Sun Comes Up)” (1993)

After the deep introspection of The Chase, his fourth album, Garth was looking to loosen up again when it came time to cut In Pieces. He turned to two of his best friends to help him get there, Blazy and Kim Williams, with whom he’d previously collaborated on the free-wheeling cheatin’ song “Papa Loved Mama” off Ropin’ the Wind. The three men were relaxing on the front porch of Blazy’s new home in Nashville when they got to talking. “We wanted to write something that was fun, for no other reason than just that: fun,” Garth said. Right there and then, they wrote this story about a girl who stays out past her curfew and winds up getting grounded because of it. “Ain’t Goin’ Down (Til the Sun Comes Up)” was a no-brainer as the album’s lead single. It didn’t disappoint by heading straight for No. 1 in September 1993.

8. “Two Piña Coladas” (1997)

If “Two Piña Coladas” seems to effortlessly evoke warm vibes and visions of relaxing on the beach, that’s no accident. The song was cut on a particularly cold and dreary day in Nashville by Shawn Camp, Benita Hill, and Sandy Mason, who wanted nothing more than to escape to someplace sunny. Not surprisingly, they figured it would be perfect for Mr. Piña Colada himself, Jimmy Buffet. However, Allen Reynolds had other ideas.

He insisted it would be a good fit for Garth, who had no trouble leaning into the party atmosphere. Garth took the song right to No. 1 when it was released as a single in March 1998. He liked the song so much that he picked up another of Hill’s compositions, “Take the Keys to My Heart,” which helped Hill pay off her credit card debt. It was a boost for Camp as well, who had another chart topper later that year with Brooks & Dunn’s “How Long Gone” and later wrote hits for Blake Shelton, Josh Turner, and George Strait.

9. “To Make You Feel My Love” (1998)

This Bob Dylan cover isn’t necessarily the most obvious choice as a Garth Brooks classic, and Garth himself agreed — at least at first. Hope Floats director Forest Whittaker and the soundtrack’s producer, Don Was, brought the song to him. They saw it as the anchor track for this romantic drama starring Sandra Bullock and Harry Connick Jr. “I don’t hear this as a Garth Brooks song,” he mused. But when Garth sat down with the lyrics, he began to appreciate its simplicity.

Dylan had released it on his late-period comeback Time Out of Mind, and Garth fave Billy Joel had already covered it. The country star gave one of his all-time great performances as a vocal interpreter, really delving into the emotional space left open by Dylan’s spare lyrics. The song served as the soundtrack opener. It was bookended by another recording of the song by none other than Trisha Yearwood. It has since become a modern standard, made more famous still by the likes of Adele.

10. “More Than a Memory” (2007)

After “To Make You Feel My Love,” the well ran dry on No. 1 hits for Garth, though it would’ve once seemed impossible to believe he’d be anywhere other than the top of the charts. In the nearly 25 years since that song was released, the country king has had just one more No. 1 single to his name, bringing his career total to 19. That came courtesy of his 2007 cut, “More Than a Memory,” one of four new songs that were recorded especially for that year’s The Ultimate Hits compilation. It debuted at No. 1, remarkably making it the first song ever to do so on the country chart, and the only one to do it based solely on radio airplay. (The metric would later be changed to include streaming figures.) The tune also marked a breakthrough for one its writers, future country hitmaker Lee Brice.

A version of this article appeared in our partner magazine Garth Brooks.