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Chris Stapleton’s ‘You Should Probably Leave’ Is an Intoxicating Ode to Doomed Love [Listen]

Chris Stapleton
Terry Wyatt, Getty Images for CMA

Chris Stapleton‘s radio singles are never straight-ahead, mainstream, made-for-radio hits. He’ll often blend an extra dose of soul or R&B into his country, and those stylistics are once again on full display in “You Should Probably Leave,” his latest submission to country radio.

Still, Stapleton wrote the song with two co-writers with serious mainstream radio cred: Chris DuBois and Ashley Gorley, the latter of whom set a record in August 2020 when he became the first songwriter ever to pen fifty No. 1 singles in the history of the Billboard Airplay and Mediabase charts (he’s continued to add to that total in the months since).

While “You Should Probably Leave” favors Stapleton’s bluesy, rootsy sensibilities over radio-ready country pop, you can also hear some of the hallmarks of a country hit: Note the complex storytelling combined with simple, repetitive phrasing, plus a surprise twist towards the end in the lyrics.

“You Should Probably Leave” tells the story of an on-again, off-again couple who can’t seem to keep themselves from coming back to one another, even though they know their story won’t end well.

‘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,” Stapleton sings in the first choruses of the song.

However, the intoxicating prospect of one more night together ultimately trumps his desire to do the right thing, and in the light of the next morning, the couple’s roles are reversed.

I want you to stay, but you’ll probably say / That you should probably leave,” he sings in the final chorus.

“You Should Probably Leave” comes off of Stapleton’s 2020 ACM Album of the Year-winning project, Starting Over, which also includes the rousing “Arkansas” as well as “Maggie’s Song,” a tribute to a beloved family dog, and “Watch You Burn,” a chilling message addressed to the shooter who killed dozens and injured hundreds more at the Route 91 Harvest Festival in Las Vegas in 2017.

However, “You Should Probably Leave” may actually be one of the older songs on Starting Over, if not the oldest song on the project outright. Wide Open Country points to a radio station performance of the song from September 2013 — before Stapleton’s rise to success as an artist, and before he released his 2015 major-label debut album, Traveller.

Did You Know?: Benmont Tench — the keyboardist and singer best known for being one of the founding members of Tom Petty and the Heartbreakers — plays Hammond B3 organ in Stapleton’s studio recording of “You Should Probably Leave.” In fact, Tench’s playing shows up several times throughout the track list of Starting Over.

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Chris Stapleton’s “You Should Probably Leave” Lyrics:

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 

There’s still time for you to finish your wine / Then you should probably leave / And it’s hard to resist, all right, just one kiss / Then you should probably leave 

Repeat Chorus

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 

Sun on your skin, six AM / And I been watchin’ you sleep / And honey, I’m so afraid you’re gonna wake up and say / That you should probably leave 

‘Cause I know you and you know me / And we both know where this is gonna lead / I want you to stay, but you’re probably say / That you should probably leave / Oh, you should probably leave

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