Vince Gill’s prodigious talent was evident early on to his contemporaries like Rodney Crowell, Guy Clark, Rosanne Cash, and Emmylou Harris. He collaborated with all of them before achieving mainstream success in the late 1980s. While it took audiences a bit longer to fully appreciate his weightless tenor voice, imbued with an almost R&B-like flexibility, they eventually caught on. Gill transitioned from being a sought-after backup singer and guitarist among artists to becoming a country music superstar. He not only achieved pop crossover success but also garnered critical acclaim, amassing more Grammy Awards than any other country artist except for his frequent collaborator, Alison Krauss.
Vince Gill performing on stage
Photo: Gustavo Caballero/Getty Images
Celebrated for his exceptional musical skills and adored by fans for his ability to convey deep emotion through ballads, Vince Gill has dedicated decades to refining his distinctive brand of neotraditional country music. This list compiles 20 of Vince Gill’s best songs, a selection that, while not fully encompassing his 21 Grammy awards, serves as an excellent starting point to explore his impressive catalog.
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20: I Will Always Love You, Something Special (1995)
When Dolly Parton decided to revisit some of her classic songs in the mid-90s, it was a natural choice to invite country music’s premier vocal powerhouse balladeer to add a fresh perspective to her most iconic song, “I Will Always Love You.” Vince Gill’s rendition brought new life to the well-known composition with his effortlessly emotive interpretation and seamless harmonies with Parton. This collaboration successfully returned the song to the country charts, reaching the No. 15 position and demonstrating the enduring appeal of both artists and the song itself.
19: What the Cowgirls Do, When Love Finds You (1994)
With “What the Cowgirls Do,” Vince Gill openly embraced the Texas two-step dance style, crafting a dancehall hit that resonated deeply with audiences. This track, far from being simplistic, incorporates a groove subtly infused with funk elements, adding a unique layer to its country foundation. Notably, the lyrics even give a shout-out to Bangor, Maine, an unexpected detail that adds to the song’s charm. Beyond its catchy rhythm, the song also highlights Gill’s guitar prowess with a signature twangy solo. “What the Cowgirls Do” climbed to No. 2 on Billboard’s country chart and became one of the most significant country hits of the year, showcasing Gill’s ability to blend traditional country sounds with contemporary sensibilities.
18: Whenever You Come Around, When Love Finds You (1994)
“Whenever You Come Around” holds a captivating backstory, contributing to its popularity and resonance. This soaring love song became Vince Gill’s biggest crossover pop hit, reaching No. 72 on the Billboard Hot 100. Adding to its allure, Trisha Yearwood provides harmonies on the track. Gill later revealed that the inspiration for “Whenever You Come Around” stemmed from his budding relationship with Amy Grant, who also appears on the album. The interesting twist was that at the time of the song’s release, Gill was still married to his first wife, Janis Oliver. This personal context added an extra layer of intrigue to the already romantic and emotionally charged song, making it a standout track in Gill’s discography.
17: I Can’t Tell You Why, Common Thread: The Songs of The Eagles (1993)
Vince Gill’s contribution to the Eagles’ tribute album, “Common Thread: The Songs of The Eagles,” with his rendition of “I Can’t Tell You Why,” charted on both the country and adult contemporary charts, highlighting its broad appeal. However, the arrangement leans significantly towards R&B, featuring a Hammond B-3 organ, a soprano saxophone solo, and Gill channeling Michael McDonald in his vocal delivery. This departure from his typical country sound was refreshing, showcasing Gill’s vocal versatility and ability to masterfully navigate different genres. The album itself was recognized as the CMA Album of the Year, with Gill’s track widely considered a standout, demonstrating his capacity to elevate even already iconic songs.
16: I Still Believe In You, I Still Believe In You (1992)
As the title track of Vince Gill’s most commercially successful album, “I Still Believe In You” set the tone for its widespread appeal. Released as the lead single, this mellow, pop-oriented ballad was intentionally produced to capitalize on country music’s increasing crossover with the adult contemporary format. It achieved its goal, becoming Gill’s first No. 1 single on the Billboard country chart and reaching No. 30 on the Adult Contemporary chart. Its genre-transcending appeal led to numerous covers, including smooth jazz and rock interpretations, proving its universal emotional resonance. The song also garnered significant critical acclaim, earning Gill two Grammy Awards and the CMA Song of the Year award for the third consecutive year in 1993, cementing its place as a landmark song in his career.
15: Pretty Words, I Still Believe In You (1992)
While “Pretty Words” is an album cut from Vince Gill’s blockbuster I Still Believe In You album, it’s far from filler. Adding to its pedigree, it’s a co-write with the renowned Don Schlitz. This track offers a refreshing and upbeat modern bluegrass sound, allowing Gill’s exceptional backing band to showcase their instrumental talents and providing Gill himself an opportunity to stretch out with an impressive guitar solo. The song’s sunny disposition and skillful musicianship, combined with a playful Monkees reference, make it a delightful and memorable deeper cut from a hugely successful album.
14: If You Ever Have Forever In Mind, The Key (1998)
“If You Ever Have Forever In Mind,” a quintessential slow-dance ballad, earned Vince Gill a Grammy for Best Male Country Vocal Performance. This award might as well have been named in his honor, as he won it nine times, including an unprecedented five consecutive years from 1995 to 1999. This particular category was retired in 2012, underscoring Gill’s dominance during its existence. “Forever,” perfect for wedding playlists, showcases Gill’s traditional crooning at its finest. The lush string section and choir arrangements almost overshadow the country elements, yet the song retains its core appeal, making it a universally beloved favorite for romantic occasions.
13: High Lonesome Sound, High Lonesome Sound (1996)
Vince Gill, always a masterful harmonizer, found a perfect vocal partner in Alison Krauss on “High Lonesome Sound.” Unsurprisingly, their collaboration earned them a Grammy Award. The single version of this Gill-penned track highlights their bluegrass expertise against a textured, almost funky arrangement, creating a unique sonic landscape. The album also features a more traditional bluegrass version of the song, backed by Krauss’s acclaimed band, Union Station, offering listeners two distinct yet equally compelling interpretations of this award-winning song.
12: Let’s Do Something, The Way Back Home (1987)
Vince Gill’s pre-MCA Records work is often overlooked, yet it contains numerous hidden gems, such as “Let’s Do Something,” a rollicking collaboration with the uncredited but unmistakable Bonnie Raitt. Gill’s bluesy undertones, more prominent in his earlier work, are evident here. While this bluesy edge became less frequent as he transitioned to mainstream country, it suits him well, especially when he showcases his impressive falsetto. “Let’s Do Something” achieved Top 20 status on the Billboard charts and, more importantly, revealed the rootsy rock influences that shaped Gill’s musical journey before his solo breakthrough.
11: Kindly Keep It Country, The Key (1998)
Released later in his career, Vince Gill’s album The Key could easily be considered an all-star duets project. Featuring collaborations with Sara Evans, Shelby Lynne, Alison Krauss, and, on “Kindly Keep It Country,” a then-emerging Lee Ann Womack, the album explored neotraditional country sounds. While “Kindly Keep It Country” wasn’t a major chart hit and carries a somewhat melancholic tone reminiscent of a sadder “Don’t Rock The Jukebox,” it’s nonetheless compelling. Featuring the inimitable pedal steel work of John Hughey and the seamless vocal blend of Gill and Womack, the song becomes a standout track, showcasing the beauty of classic country instrumentation and vocal harmonies.
10: Tryin’ To Get Over You, I Still Believe In You (1994)
“Tryin’ To Get Over You” marks Vince Gill’s most recent solo country chart No. 1 hit. Solely written by Gill, it’s a poignant heartbreak song exploring themes of loss and longing, echoing the emotional depth of classics like “He Stopped Loving Her Today.” The song’s anthemic chorus builds without fully becoming a power ballad, allowing space for Gill’s elastic vocal range and gentle vibrato, as well as John Hughey’s signature pedal steel work, to shine. It became a perfect concert moment for Gill, then reigning CMA Entertainer of the Year, to connect with audiences through shared emotions of heartbreak and resilience.
9: Liza Jane, Pocket Full Of Gold (1991)
Vince Gill put his unique rockabilly spin on the traditional New Orleans folk song “Liza Jane,” transforming it into a fun, danceable single that reached No. 7 on Billboard’s country chart. Retro yet fresh, it represents a more flirtatious and playful side of Gill’s artistry during his peak popularity. The song’s appeal lies in its come-hither vibe, Gill’s virtuosic guitar solo, and Andrea Zonn’s spirited fiddle playing, creating an infectious and energetic track.
8: Oklahoma Borderline, The Things That Matter (1985)
Starting his career as a highly sought-after session vocalist and guitarist gave Vince Gill access to top-tier collaborators throughout his career. Even on his debut album, Gill worked with Rosanne Cash and, for “Oklahoma Borderline,” enlisted Rodney Crowell and Guy Clark as co-writers. Having previously played in both Crowell’s and Clark’s bands, their contribution to “Oklahoma Borderline” was a natural reciprocation. The result is a bright, upbeat, and witty tribute to Gill’s Oklahoma roots, replacing his usual sentimentality with energy and humor, showcasing a different facet of his artistry early in his solo career.
7: Pocket Full Of Gold, Pocket Full Of Gold (1991)
“Pocket Full Of Gold” places Vince Gill in his element: delivering a heartfelt vocal performance alongside Patty Loveless in a melancholic country waltz. Stripped down and traditionally arranged, it’s also one of Gill’s singles that prominently features the wordplay characteristic of classic country songs. The song’s central metaphor – the “gold” in the title – is readily understood as tears or heartache, yet this predictability doesn’t diminish the emotional impact and satisfaction of the chorus, highlighting the power of simple yet resonant country storytelling.
6: One More Last Chance, I Still Believe In You (1993)
Vince Gill contributed to the two-step revival with “One More Last Chance,” an upbeat roadhouse-ready track featuring Delbert McClinton on harmonica and a taste of Gill’s exceptional guitar playing. The music video includes a cameo by George Jones, whose legendary antics, including riding-lawnmower incidents, served as partial inspiration for the song, co-written by Gill and Gary Nicholson. Interestingly, the video begins and ends on a golf course, referencing Gill’s almost-career path as a professional golfer, adding a personal and humorous touch to this lively country tune.
5: Which Bridge To Cross (Which Bridge To Burn), When Love Finds You (1994)
There is a timeless quality to “Which Bridge To Cross (Which Bridge To Burn).” Its beauty lies in its traditional country waltz structure. Co-written by Vince Gill with Nashville songwriting icon Bill Anderson, the song’s success, reaching No. 4 on Billboard’s country chart, helped revitalize Anderson’s career. The vocal harmonies showcase Gill at his goosebump-inducing best, and the song in its entirety embodies simple, heartfelt country music at its finest, emphasizing emotion and classic songwriting.
4: Look At Us, Pocket Full Of Gold (1991)
Part of Vince Gill’s remarkable hat trick of consecutive CMA Song Of The Year awards, “Look At Us” is a tender love song seemingly crafted for anniversaries. However, instead of becoming overly sentimental, Gill creates a poignant duet with John Hughey’s expressive steel guitar, lending the track a vibrant vintage feel. While Gill became known as country’s favorite crooner with some ballads that haven’t aged as gracefully, “Look At Us” stands the test of time. Its spacious arrangement allows the traditional country instrumentation to shine, creating a lasting and genuine emotional impact.
3: Don’t Let Our Love Start Slippin’ Away, I Still Believe In You (1992)
“Don’t Let Our Love Start Slippin’ Away” injects energy and danceability into Vince Gill’s catalog. A playful rebuke to fading romance, this song spent three weeks at the top of Billboard’s country chart, becoming Gill’s biggest hit to date. It provided a necessary upbeat contrast to the ballad-heavy I Still Believe In You album, which achieved five-times platinum certification. The song’s all-star music video, though not readily available online, featured a wide array of artists from Michael McDonald and Leon Russell to Reba McEntire and Pam Tillis, enjoying heavy rotation on CMT and further cementing the song’s popularity.
2: Go Rest High On That Mountain, When Love Finds You (1995)
One of Vince Gill’s signature songs, “Go Rest High On That Mountain,” is also among his most emotionally resonant. Rolling Stone even ranked it as the 17th saddest country song of all time, a category filled with intense competition. This hymn-like eulogy, written by Gill in honor of both Keith Whitley and his brother Bob, was released during the AIDS pandemic, a time marked by many elegiac pop hits. “Go Rest High On That Mountain” dominated the 1996 awards season, winning two Grammys, the CMA Award for Song of the Year, and a BMI Most-Performed Song award. Featuring backing vocals from Ricky Skaggs and Patty Loveless, and Stuart Duncan’s mournful fiddle, the song transcends its accolades. It has become a funeral standard; Gill’s emotional performance of it at George Jones’ funeral in 2013, where he struggled to sing the lyrics, underscores its profound and enduring impact.
1: When I Call Your Name, When I Call Your Name (1990)
While not Vince Gill’s first or biggest chart hit, “When I Call Your Name” marked his mainstream breakthrough. It earned him his first Grammy and CMA awards, even amidst Garth Brooks’s rise to stardom in the same year. Listening to it now, it’s clear why this track captured Nashville’s attention. Tony Brown’s neotraditional production, a departure from previous styles, combined with the perfect blend of Gill’s and Patty Loveless’s voices, transforms this slow-burning waltz into a breathtaking showcase of Gill’s impeccable tenor. Co-written by Gill, “When I Call Your Name” embodies country music classicism, featuring a piano solo from Muscle Shoals legend Barry Beckett and pedal steel from Nashville stalwart Paul Franklin. However, it’s the song’s key change that consistently delivers chills, solidifying its place as Vince Gill’s quintessential song.
Do you think we overlooked one of Vince Gill’s best songs? Share your thoughts in the comments below.
