Nashville is a city of prolific songwriters with catalogs of unreleased, potentially classic songs. “You Should Probably Leave” has been banging around town since 2014, and YouTube is full of old clips showing Chris Stapleton performing it.
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The song was intended for his debut album on Mercury Nashville. But the lead single didn’t fare well, and the album was shelved. Stapleton tried again; this time, he released Traveller in 2015, earning a CMA Award for Album of the Year.
Born in Lexington, Kentucky, Stapleton moved to Nashville to study engineering at Vanderbilt University. With an instinct for hooks and a divine singing voice, the music business pulled him away from his studies, and Stapleton dropped out of college, signed a publishing deal, and began writing songs for other artists to record.
Traveller is a fitting title for Stapleton’s debut. In 2007, he joined the SteelDrivers, where he had two hit records with the bluegrass group before leaving to form a Southern rock band called the Jompson Brothers. But something kept pushing Stapleton to move on again. His voice proved to be too big to be part of an ensemble.
By 2013, he signed to Mercury as a solo artist. In hindsight, destiny was at play in Stapleton’s life, though it surely didn’t feel that way to him. As the music business tried to pummel him with fits and starts, Stapleton kept singing and writing songs. He eventually traveled to the place where destiny meets stubborn will.
The Old Song Just Kept Hangin’ Around
Stapleton wrote the song with fellow Nashville writers Chris DuBois and Ashley Gorley. After the false start with his pre-Traveller debut, “You Should Probably Leave” didn’t make the cut for three albums. Stapleton’s wife, Morgane, convinced him in 2020 to include it on his then-new album, Starting Over.
The song follows a conversation between two former lovers. As they reenter each other’s lives, he tells her they shouldn’t give in to temptation because they know how this ends.
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
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By the song’s end, they’ve spent the night together, and the script flips where he’s hoping she won’t wake up with regret and ask him to leave.
Sun on your skin, 6 a.m.
And I been watchin’ you sleep
And honey, I’m so afraid you’re gonna wake up and say
That you should probably leave
Stapleton’s music sounds easy, even when singing about a messy relationship. People talk about how smooth a particular whiskey is, but it’s only smooth after the body has grown tolerant of the burning fire washing down the throat. “You Should Probably Leave” sounds like smooth whiskey, where life’s challenges have broken the soul, creating a kind of thick skin for damaged relationships.
’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
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The Heartbreakers
Two Heartbreakers joined Stapleton on Starting Over. Guitarist Mike Campbell and keyboardist Benmont Tench contributed to the sessions, though Stapleton handled guitar duties on “You Should Probably Leave.” Morgane Stapleton sings backing vocals on the album, and her steady voice isn’t just supporting her husband, it hums reassuringly against Stapleton’s husky delivery. Stapleton is joined by longtime producer Dave Cobb, who, for years, has been reliably making some of Nashville’s finest albums.
Was It Worth the Wait?
The world was learning to live with the pandemic the year Stapleton released Starting Over. Though people weren’t prepared to return to the office, they were ready for a new Stapleton album. He won a Grammy Award for Best Country Album, and “You Should Probably Leave” won a Grammy for Best Country Solo Performance. It became his third No. 1 country single.
Stapleton’s first attempt at a debut had failed. Then he tried again and turned the country music world on its ear. Six years after writing “You Should Probably Leave,” he rediscovered an old song deserving another chance, like the couple in the song searching for a new beginning.
The failed single from Stapleton’s first swing at a solo career is called “What Are You Listening To?” In hindsight, it doesn’t sound like him. Stapleton might have had a short career from a quick start in a parallel universe where “What Are You Listening To?” does well. But he needed a little age, like the whiskey mentioned earlier.
What Chris Stapleton needed was a slow burn.
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