Lainey Wilson & ERNEST Reawaken “Would If I Could”

Lainey Wilson and ERNEST’s duet “Would If I Could” is a modern classic in waiting: a 1990s-shaped ballad written nearly three decades ago by legendary songwriters Dean Dillon and Skip Ewing, revived for ERNEST’s 2024 album NASHVILLE, TENNESSEE and now blooming on Wilson’s 2025 Whirlwind tour. The result pairs time-tested writing with two of country’s most distinctive contemporary voices, proof that a great song only needs the right moment to find its people.

Watch the recent live clip!

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

Quick Facts: “Would If I Could”

• Artists: ERNEST & Lainey Wilson
  
• Songwriters: Dean Dillon, Skip (Donald) Ewing
  
• First Lainey recording: 2023 Apple Music Sessions (solo)
  
• Duet release: April 12, 2024, on ERNEST’s NASHVILLE, TENNESSEE
  
• Live momentum: Performed together at special sets and as part of Wilson’s Whirlwind tour dates in 2025
  
• Common search term: “What If I Could” (frequent misspelling of the title)
  

The Song’s Journey: From a One-Off Writing Session to a Signature Duet

“Would If I Could” has an origin story that hardcore country fans love. Dean Dillon and Skip Ewing, two hall-of-fame-caliber craftsmen, wrote the song in 1996 in what’s been described as their only collaboration together. For years, the ballad lived quietly on the shelf, admired but uncut, until Wilson and ERNEST discovered it and brought it forward with reverence.

Wilson first cut the song solo for an Apple Music Sessions set in late 2023, highlighting its plainspoken heartbreak and classic Nashville melody. Months later, ERNEST released the duet version on his 26-track project NASHVILLE, TENNESSEE, deepening the conversation between the voices and putting a spotlight back on the craftsmanship of the ’90s.

Why “Would If I Could” Hits So Hard

• Classic country DNA: Lyrical simplicity, conversational phrasing, and a melody built for a hardwood honky-tonk floor.
  
• Dual-narrative storytelling: ERNEST and Wilson trade lines with the tenderness and tension of two people who want the same thing, just not at the same time.
  
• Vocal chemistry: Wilson’s earthy, bell-clear tone lifts ERNEST’s warm baritone; together they land in that sweet spot between traditional and today.
  
• Rescue & revival: The track shows how catalog gems can become current when the right artists give them oxygen.
  

Live: From Bluebird Magic to the Whirlwind Tour

The duet has had a life both intimate and arena-ready. ERNEST and Wilson previewed it together in writer-room settings, including a sweet moment at Nashville’s Bluebird Café, and are now delivering it on big stages as Wilson’s Whirlwind tour rolls across 2025, with ERNEST appearing as a special guest on select dates. The contrast, pin-drop rooms vs. roaring arenas, only underscores how sturdy the song is.

Live Performance Highlights

• Stripped arrangements that spotlight two voices and the lyric
  
• Emphasis on dynamic phrasing over vocal fireworks
  
• Audience response shaped by recognition (fans of Wilson’s 2023 version) and discovery (new listeners coming in via ERNEST’s album)
  

Inside the Lyric: Love, Timing, and the Things We Can’t Force

At its core, “Would If I Could” is about loving someone you can’t keep, and having the emotional intelligence to say so. That balancing act of compassion and boundaries is what gives the song its grown-up ache. No finger-pointing, just two people acknowledging that desire and timing don’t always align. It’s country music’s oldest truth told with fresh humility. 

The Record: Where to Find It (and Why This Cut Matters)

• Album home: NASHVILLE, TENNESSEE (ERNEST, 2024)
  
• Streaming: Available on major platforms (Apple Music, Spotify, YouTube)
  
• Reception: Celebrated by critics and fans for its throwback feel and “duet perfection.”
  

Credits & Context

• Songwriters: Dean Dillon, Skip Ewing
  
• Artists: ERNEST (feat. Lainey Wilson) on album version; Lainey Wilson solo cut (2023 Apple Music Sessions)
  
• Era & vibe: Mid-’90s melody, 2020s polish, bridging traditional storytelling with contemporary production touches
  

FAQ: “Would If I Could” vs. “What If I Could”

Is the title “What If I Could”?
No, the official title is “Would If I Could.” Listeners often mis-search it as “What If I Could,” so you’ll see both phrasings discussed online. Using the correct title will help you find the duet on ERNEST’s album and Wilson’s 2023 session cut.