Lainey Wilson And Ernest Team Up For Beautiful Duet Of Their Classic Country Heartbreaker, “Would If I Could”

Timeless country music.

This weekend, Lainey Wilson is back out on the road for her extensive Whirlwind tour, which includes Ernest as an opener and if you have him opening any of your shows, you’re lucky, because they’re giving fans a beautiful performance of his classic country heartbreaker “Would If I Could.”

The song was included on Ern’s Nashville, Tennessee album that he released earlier this year as a duet with Lainey, and it actually has an incredibly interesting backstory, seeing as it was written in 1996 by two of the all-time great country music songwriters Dean Dillon and Skip Ewing in what was somehow their only writing collaboration together.

He sent a solo version to country radio because Lainey had at least one other single starting to take off at radio, but nothing beats the duet version in my humble opinion.

It’s already stood the test of time, because the song is actually almost 30-years old. A little while back, legendary songwriter Dean Dean told Lost & Found Radio with Lori McKenna that he always knew it was a great song that for whatever reason just got tossed aside like so many unfortunately do:

“Skip and I had never written before, I don’t know who had the melody or who had the idea, but when we finished, I thought we had a great song.

There was more to it than a lot of other stuff I’ve written, but for whatever reason, and you know this yourself, it happens a lot. They just get pitched a couple times and that’s it. You never hear about them again. And then somebody somewhere dug this out of the trash can somewhere.”

Lainey actually first covered “Would If I Could” solo for a special Apple Music Sessions feature in 2023, and I was obsessed from the very first time I heard it. So when Ernest announced that they were turning it into a duet for his aforementioned project, I knew it would be special because it’s such a timeless and beautiful song. Classic is the word that comes to mind every time I hear it, which is a huge compliment especially in the music industry in 2025.

With a melody that’s stood the test of time for almost three decades, Ernest and Lainey brought a fresh sound with their modern vocals, which shine as they sing about heartbreak and knowing when it’s time to let go of a relationship… even if you’d rather do anything else.

In my initial post about the song, I said that the song sounds like it could be playing at an old hole in the wall honky tonk in 1974, and the simplicity and honesty in every verse just cuts straight to the heart. Plus, Lainey gets to show off her incredible pipes since they’re playing a pretty stripped back version onstage, and I can’t get enough. This weekend might be the first time they’ve played it together live before, and I’m just so glad they’re giving it the attention and shine it deserves.

Ernest and Lainey both have a deep respect for the roots and tradition of the genre, and I will forever be mad “Would If I Could” didn’t become a huge hit. The best ones usually don’t, though, unfortunately…

These kinds of songs are what set country apart from every other genre, and in my very humble opinion, you cannot beat a sad, simple heartbreaker like this one. It’s perfect and their live performance is just stunning:

@maddygreeeen probably one of my favorite parts of the entire concert. they sounded so good together!! #laineywilson #ernest #phx1 #country ♬ original sound – mads

“Would If I Could”

LAINEY WILSON CONFIRMED TOUR DATES:

August 14—Phoenix, AZ—Footprint Center*
August 15—Albuquerque, NM—Isleta Amphitheater*
August 16—Denver, CO—Ball Arena*
August 21—Bend, OR—Hayden Homes Amphitheater*
August 22—Sacramento, CA—Golden 1 Center*
August 23—Los Angeles, CA—Kia Forum*
August 28—Calgary, AB—Scotiabank Saddledome*
August 29—Edmonton, AB—Rogers Place*
August 30—Saskatoon, SK—SaskTel Centre*
September 11—Baton Rouge, LA—Raising Cane’s River Center†
September 13—Bossier City, LA—Brookshire Grocery Arena†
September 18—Austin, TX—Moody Center‡
September 19—Fort Worth, TX—Dickies Arena‡
September 20—Houston, TX—The Cynthia Woods Mitchell Pavilion presented by Huntsman ‡
September 25—Toronto, ON—Budweiser Stage§
September 26—Clarkston, MI—Pine Knob Music Theatre§
September 27—Grand Rapids, MI—Van Andel Arena§
October 2—Nashville, TN—Bridgestone Arena||
October 3—Noblesville, IN—Ruoff Music Center§
October 4—Cleveland, OH—Blossom Music Center§
October 9—Columbia, MD—Merriweather Post Pavilion§
October 10—New York, NY—Madison Square Garden§
October 11—Mansfield, MA—Xfinity Center§
October 16—St. Louis, MO—Hollywood Casio Amphitheatre||
October 17—Rosemont, IL—Allstate Arena||
October 18—Saint Paul, MN—Xcel Energy Center||
October 24—Knoxville, TN—Thompson-Boling Arena at Food City Center#
October 25—Charlotte, NC—Spectrum Center#
November 7—Tampa, FL—Amalie Arena#
November 8—Orlando, FL—Kia Center#

~with special guest Zach Meadows
*with special guests ERNEST and Kaitlin Butts
†with special guests ERNEST and Maddox Batson
‡with special guests Muscadine Bloodline and Drake Milligan
§with special guests Muscadine Bloodline and Lauren Watkins
||with special guests Muscadine Bloodline and Maddox Batson
#with special guests ERNEST and Drake MilliganThe post Lainey Wilson And Ernest Team Up For Beautiful Duet Of Their Classic Country Heartbreaker, “Would If I Could” first appeared on Whiskey Riff.