Chris Stapleton, born April 15, 1978, in Lexington, Kentucky, is a well-known American country singer-songwriter and guitarist who mixes country, rock, blues, and soul in his music.
After moving to Nashville to study engineering, he left college to focus on songwriting, creating over 170 songs and six number-one country hits for artists like Kenny Chesney, George Strait, and Luke Bryan.
Before his solo work, Stapleton was lead vocalist for the bluegrass band the SteelDrivers and later the Southern rock band the Jompson Brothers.
His 2015 solo album, Traveller, was hugely successful, winning multiple Grammy, CMA, and ACM awards, and included the diamond-certified “Tennessee Whiskey.”
His albums From A Room: Volumes 1 & 2, Starting Over, and Higher have earned him eleven Grammy Awards total.
About the Song
“You Should Probably Leave” is a soulful country ballad by Chris Stapleton, released as the third single from his 2020 album Starting Over.
Written by Stapleton, Ashley Gorley, and Chris DuBois, the song tells the story of an on-again, off-again couple struggling with temptation and the inevitable heartbreak that follows their recurring encounters.
With Stapleton’s signature bluesy vocals and honest storytelling, the track explores the tension between desire and doing the right thing, resonating with listeners through its emotional depth and relatable narrative.
The song earned Stapleton the Grammy Award for Best Country Solo Performance in 2022.
| Details | Information |
|---|---|
| Released | Nov. 13, 2020 |
| Album | Starting Over |
| Genre | Country |
| Writers | Chris Stapleton, Ashley Gorley, Chris DuBois |
| Producer | Dave Cobb, Chris Stapleton |
| Length | 3:33 |
You Should Probably Leave Lyrics
[Verse 1]
I know it ain’t all that late
But you should probably leave
And I recognize that look in your eyes
Yeah, you should probably leave
[Chorus]
‘Cause I know you and you know me
And we both know where this is gonna lead
You want me to say that I want you to stay
So you should probably leave
Yeah, you should probably leave
[Verse 2]
There’s still time for you to finish your wine
Then you should probably leave
And it’s hard to resist, alright, just one kiss
Then you should probably leave
[Chorus]
‘Cause I know you and you know me
And we both know where this is gonna lead
You want me to say that I want you to stay
So you should probably leave
Yeah, you should probably leave
[Bridge]
Like a devil on my shoulder, you keep whisperin’ in my ear
And it’s gettin’ kinda hard for me to do the right thing here
I wanna do the right thing, baby
[Verse 3]
Sun on your skin, 6AM
And I been watchin’ you sleep
And honey, I’m so afraid you’re gonna wake up and say
That you should probably leave
[Chorus]
‘Cause I know you and you know me
And we both know where this is gonna lead
I want you to stay but you’ll probably say
That you should probably leave
Yeah, you should probably leave
Oh, you should probably leave
You Should Probably Leave Lyrics Meaning
[Verse 1]
I know it ain’t all that late….probably leave
Meaning: The singer senses the tension in the air as his former lover visits him. Though it’s still early in the evening, he feels a familiar pull between them and recognizes the longing in her eyes.
He knows from experience that if she stays any longer, they’ll give in to old habits and desires, leading to the same emotional pain they’ve felt before.
Even though the temptation is strong, he gently suggests she should leave before things go too far.
[Chorus]
‘Cause I know you and you….probably leave
Meaning: In the chorus, both the singer and his lover share a deep understanding of each other.
They know exactly where the night is headed if she doesn’t leave-they’ll end up together again, repeating a cycle that always ends in regret.
She silently wishes he’d ask her to stay, hoping for a different outcome, but he cares enough to be honest. He insists she should leave, trying to protect them both from making the same mistake again.
[Verse 2]
There’s still time for you to finish….probably leave
Meaning: As the night progresses, he offers her time to finish her wine, subtly delaying the inevitable goodbye.
The attraction between them is undeniable, and the idea of sharing just one kiss is almost impossible to resist. Yet, he knows that giving in, even for a moment, will only make things harder.
He struggles with his feelings, torn between desire and wisdom, but ultimately urges her to leave before they cross a line they’ll both regret.
[Bridge]
Like a devil on my shoulder….right thing, baby
Meaning: In the bridge, the singer compares her presence and words to a devil on his shoulder, tempting him to ignore what he knows is right.
Her whispers make it increasingly difficult for him to resist, and he admits how hard it is to do the right thing when his feelings are so strong.
He’s caught in a battle between his heart and his conscience, desperately wanting to make the right choice even though it hurts.
[Verse 3]
Sun on your skin….probably leave
Meaning: The scene shifts to the morning after, with sunlight streaming in as he quietly watches her sleep. Now, the roles are reversed-he’s afraid she’ll wake up, realize what’s happened, and feel the need to leave.
There’s a sense of vulnerability and regret as he contemplates the consequences of their actions.
He wishes things could be different but knows deep down that they’re stuck in a cycle that’s hard to break.
Themes of the Song
“You Should Probably Leave” by Chris Stapleton tells a story that many can relate to – the push and pull between what we want and what we know is right.
The song brings to life the inner conflict that comes with complicated relationships.
- Conflicted Attraction: Former lovers drawn together despite knowing better.
- Bad Timing: Caught in a repeating cycle of reunion and separation.
- Temporary Pleasure vs. Long-term Pain: The battle between wanting one night together versus avoiding future heartbreak.
- Self-Awareness: Both people recognize their pattern but struggle to break free.
The beauty of Stapleton’s writing is how it captures this all-too-human tendency to make choices we know aren’t good for us, especially when it comes to matters of the heart.
Awards and Nominations for You Should Probably Leave
Chris Stapleton’s soulful ballad has gained not just fan admiration but also formal recognition from the music industry. The song has collected several honors since its release:
| Award Ceremony | Year | Category | Result | Notes |
|---|---|---|---|---|
| Grammy Awards | 2022 | Best Country Solo Performance | Won | Stapleton’s sixth Grammy overall, praised for soulful delivery |
| Grammy Awards | 2022 | Best Country Song | Nominated | Recognized for songwriting excellence |
| Academy of Country Music (ACM) Awards | 2023 | Song of the Year | Nominated | Also nominated as songwriter and performer |
| Academy of Country Music (ACM) Awards | 2023 | Single of the Year | Nominated | Multiple nominations for this song |
| American Music Awards | 2022 | Favorite Country Song | Nominated | Acknowledged among top country songs of the year |
| All-American Roadshow Awards (AIMP) | 2023 | Song of the Year | Won | Award shared with co-writers Ashley Gorley and Chris DuBois |
Chris Stapleton’s “You Should Probably Leave” has been widely acclaimed, earning him a Grammy win and multiple nominations at prestigious country music awards, highlighting both his vocal performance and songwriting skills
You Should Probably Leave Live Performance
Chris Stapleton – You Should Probably Leave (Live From Show Concert Series)
You Should Probably Leave (Live From The Show Starring Jimmy Fallon)
Kellyoke – You Should Probably Leave
Popular Albums by Chris Stapleton
Chris Stapleton has built an impressive catalog of music that shows his skill as both a singer and songwriter. Here’s a look at his most successful albums that have won fans and critics alike:
1. Starting Over (2020): A collection of songs about renewal and moving forward, blending country roots with blues and rock influences across 14 thoughtful tracks.
2. Traveller (2015): Stapleton’s breakthrough solo album featuring rich vocals and honest storytelling that brought traditional country sounds back to mainstream popularity.
3. From A Room: Volume 1 (2017): A raw, stripped-down album recorded at historic RCA Studio A that showcases Stapleton’s powerful voice and authentic songwriting approach.
4. From A Room: Volume 2 (2017): The companion to Volume 1, offering more intimate, soulful tracks that continue the organic sound while exploring themes of love, loss, and personal struggle.
Join us as we look at what famous artists truly want to say through their music. Find your next favorite song lyrics and meaning and what makes it special.
Frequently Asked Questions
What is the Theme of The Song “Starting Over” by Chris Stapleton?
The song focuses on new beginnings, taking chances, and finding hope through change with someone you love despite life’s uncertainties.
Is Starting Over by Chris Stapleton a Good Wedding Song?
Yes, it works well for couples who value fresh starts and facing life’s changes together, though it’s less traditional than typical wedding songs.
Did Chris Stapleton Write a Song for His Wife?
Yes, Chris Stapleton wrote “Tennessee Whiskey” with his wife Morgane in mind, and they often perform it together during concerts.
Kelsey Roberts is an accomplished songwriter with a knack for crafting lyrics that resonate with listeners. Having written for both indie artists and major labels, Kelsey brings a deep understanding of what makes a song truly impactful. Her expertise includes everything from song structure to lyrical storytelling. She’s passionate about helping others discover their voice through songwriting, providing tips and inspiration for creating songs that touch hearts.
