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The Best Vince Gill Songs

July 25, 2023 3:42 pm GMT

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Vince Gill is one of the finest triple threats in country music. He’s a virtuosic guitarist, impeccable songwriter and stellar vocalist who, over the span of his multi-decade career, has notched 22 Grammy Awards, 18 CMA Awards and 8 ACM Awards.

Gill has also offered his musical talents to groups such as The Time Jumpers, the Eagles and Pure Prairie League, and collaborated with the likes of Patty Loveless, Carrie Underwood, Sara Evans and fellow Okie Reba McEntire.

To celebrate Gill’s timeless catalog, here are 15 of his best songs, as ranked by Holler.

15
MCA | 2019

Forever Changed

Solely penned by Gill, the heart-on-sleeve ‘Forever Changed’ finds him narrating an awful case of sexual abuse. “She feels dirty / She feels ashamed / Because of you / She's forever changed”, he sings in the chorus. Though it’s written from a female victim’s perspective, Gill shared that the account stemmed from his real-life childhood experience.

14
MCA | 2019

When My Amy Prays

Gill gets real about faith, prayer and steadfast love in ‘When My Amy Prays’. The track, which nabbed a Grammy for Best Country Solo Performance in 2019, has Gill expressing both humility and gratitude for his wife Amy Grant. “When my Amy prays / When my Amy prays / That's when I see his face,” he professes.

13
MCA | 2016

I'll Be Waiting for You (ft. Cam)

This stunning ballad from 2016’s Down to My Last Bad Habit portrays the persona’s post-breakup state and how he’s still pining for his ex’s return. Gill’s warm vocals and CAM’s ethereal harmonies beautifully amplify this melancholy sentiment and make the wistfulness almost palpable.

12
MCA | 1998

My Kind of Woman/My Kind of Man

“You're my kind of woman, you're my kind of man / A match made in Heaven by God's gentle hands / I'll love you forever, together we'll stand / You're my kind of woman, you're my kind of man,” Gill and Loveless confess in the chorus with their friendship chemistry taking center stage. This same friendship from 1999 is still going strong today.

11
MCA | 2019

I Don't Wanna Ride the Rails No More

One of the standouts on 2019’s Okie, this heartfelt tune chronicles Gill’s thoughts on chasing a dream and settling down. Here, the singer’s done “hoppin’ freight trains all my life” and instead, opts to hang up his boots, be still and find contentment in what he already has.

“I don't wanna ride the rails no more / I wanna know a woman's love worth dyin' for / Hear children playin' through an old screen door / No, I don't wanna ride the rails no more,” Gill renders over a steady train track-like rhythm.

10
MCA | 1989

Oklahoma Swing

The second single off When I Call Your Name, ‘Oklahoma Swing’ is a spirited Western swing number that finds Gill and Reba McEntire playfully flirting on a song as lovers. Perfectly melding tradition with tempo, it’s unquestionably one of Gill's finest compositions yet.

9
MCA | 1994

Which Bridge to Cross (Which Bridge to Burn)

“I knew this was wrong, I didn't listen / Cause a heart only knows what feels right”, Gill laments as he regretfully reflects on his two-timing ways.

“I'm standing at the crossroads with just one concern / Which bridge to cross and which bridge to burn,” he continues. If you’ve found yourself caught between two lovers, this one’s for you.

8
MCA | 2003

Next Big Thing

The title track and lead single off 2002’s Next Big Thing, this upbeat offering has Gill bouncing around as he observes the ever-changing world before him. Gill’s not quite the “next big thing” yet, but he’s pining to be someone universally adored.

“I'll get a cowboy hat / Some real tight jeans / Lose a little weight and / Get a belly button ring,” declares Gill. “Big cigars, diamond rings / Ridin' all around in a limousine / When you finally hit the top / Man you know what that means / Everybody's ready for the next big thing”, he continues in the jaunty chorus.

7
MCA | 1991

Look at Us

As soon as the wailing pedal steel instrumentation arrives, you know you’re about to be served up a classic country tune. This pristine ballad was co-written by Gill and chronicles a relationship that’s weathered the storms of life. “When they wanna see / How true love should be / They'll just look at us,” he posits gently in the chorus.

6
MCA | 1995

The Heart Won't Lie

'The Heart Won’t Lie' is indisputably one of the most iconic 90s duets. While the original plan was to have Gill provide harmonies, McEntire’s longtime producer Tony Brown suggested he go solo on a verse — which proved to be a hit-making decision. Coupled with a movie-like music video, 'The Heart Won’t Lie' became McEntire’s 17th chart-topper and Gill’s third.

5
MCA | 1989

When I Call Your Name

One of Gill’s most well-known songs, this timeless, tear-soaked ballad finds him recounting the heartbreak he was unexpectedly thrust into.

“Oh, the lonely sound of my voice calling / Is driving me insane / And just like rain, the tears keep falling / But nobody answers when I call your name,” Gill sings in the searing chorus as a reservoir of emotions well up.

4
MCA | 1992

Don't Let Our Love Start Slippin' Away

Gill does an excellent job of balancing a heartbreak narrative with a feel-good delivery in this jovial, sing-along tune. Let’s not forget the wise relationship advice offered, too. “Real love walks a real thin line / No communication will kill it every time,” shares Gill.  Ain’t that the truth, y’all?

3
MCA | 1994

Whenever You Come Around

This romantic ode describes a man’s longing to be together with an enchanting woman who’s got a “face like an angel” and “pretty eyes that shine.” Unfortunately, fate has it otherwise and he’s left with “the biggest heartache in town.” Exquisite harmonies are provided by fellow country icon Trisha Yearwood, as well.

2
MCA | 1992

One More Last Chance

Over a euphoric production, Gill begs for “one more last chance” to make things right with his love interest, albeit with a cheeky grin. As his plea continues, so does the song’s hooky, toe-tapping production that’ll get fans singing along in no time.

1
MCA | 1994

Go Rest High on That Mountain

A common fixture at funerals in the country music community, this poignant 1994 ballad finds Gill delivering heartfelt words as he mourns the loss of someone near and dear to him. In 2013, the singer and Loveless took the Grand Ole Opry stage together to deliver a tear-jerking performance of the song at George Jones’ funeral.

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Listen and subscribe to Holler's The Best Vince Gill Songs playlist now:

For more on Vince Gill, see below:

Written by Jeremy Chua
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