A Song That Took Seven Years to Find Its Moment

Chris Stapleton has built a career around songs that often feel timeless, and “You Should Probably Leave” is one of the clearest examples of that approach.

The song was written years before it became a major release. Stapleton co-wrote it with Ashley Gorley and Chris DuBois in 2014, long before audiences would hear it as a single from his album Starting Over.

That long journey makes the song’s continued success particularly interesting.

What began as a song written in Nashville eventually became one of Stapleton’s most recognizable recordings. It was later released as the third single from Starting Over, and its success helped add another important chapter to Stapleton’s career.

The song also earned Stapleton a Grammy Award for Best Country Solo Performance at the 2022 Grammy Awards. His official website confirms the win, which came during a ceremony where he collected three Grammy Awards in total.

Written in 2014

One of the most fascinating details about “You Should Probably Leave” is that it existed for years before becoming a major commercial release.

Stapleton, Gorley, and DuBois wrote the song in 2014.

At that point, it was simply another piece of songwriting created during a productive period in Stapleton’s career.

The song would eventually become part of Starting Over, but the recording process and release came years after the original writing session.

That kind of delay is not unusual in Nashville.

Songwriters frequently create material that may remain unreleased for months or even years. Some songs are recorded by different artists, some are rewritten, and others simply wait until the right album or moment arrives.

“You Should Probably Leave” turned out to be a song worth waiting for.

An Early Performance With Morgane

Before the song became widely known, Stapleton performed it in a much smaller setting.

Footage from October 2014 shows Chris Stapleton performing the song in Nashville, with his wife, Morgane Stapleton, joining him.

The early performance provides an interesting glimpse into the song before it became a major single.

There is something striking about seeing a song in such an early form, before it has reached radio audiences, major award ceremonies, or millions of listeners.

The performance also highlights the importance of live music in Stapleton’s career.

His music has often been presented in a way that places the songwriting and vocals at the center of the experience rather than relying entirely on elaborate production.

The Song Finally Arrived on Starting Over

Years after it was written, “You Should Probably Leave” became part of Stapleton’s fourth studio album, Starting Over.

The album was released in 2020 and quickly became an important project in his career.

Rather than rushing the song into the marketplace simply because it had existed for several years, Stapleton waited until it fit the direction of the album.

The result was a recording that combined contemporary country production with the blues, soul, and roots influences that have become closely associated with Stapleton’s sound.

The song eventually became the third single from the album.

That detail is worth noting because it was not positioned as the lead single.

It did not need to be the first song released from the project to establish a lasting connection with listeners.

A Major Success Without a Traditional Music Video

Another unusual part of the song’s story is that it did not receive an official music video.

In an era when visual content is an important part of promoting a single, the song was able to build a significant audience without relying on a traditional official video.

Instead, its success was driven by the recording itself, radio play, streaming, live performances, and word of mouth.

That is an important reminder that a song does not always need a large visual campaign to connect with listeners.

Strong songwriting and a memorable performance can sometimes carry a recording much further than expected.

Grammy Recognition in 2022

The song’s impact was also recognized by the recording industry.

At the 64th Annual Grammy Awards in 2022, “You Should Probably Leave” won the award for Best Country Solo Performance.

Stapleton’s official website confirms that he won three awards at that ceremony. In addition to the solo performance award for “You Should Probably Leave,” he won Best Country Album for Starting Over and Best Country Song for “Cold.”

Winning a Grammy added another significant achievement to the song’s already unusual history.

A composition written in 2014 had taken years to become a major release, and then went on to receive one of the most prestigious honors in recorded music.

The Appeal of the Song

Part of the appeal of “You Should Probably Leave” comes from its simple but recognizable premise.

The song tells the story of two people who know exactly where their attraction could lead, even though they understand that continuing the situation may not be the best decision.

That tension gives the song a conversational quality.

Rather than presenting an overly complicated story, the writing focuses on a familiar human situation: knowing that someone should leave while secretly hoping they stay.

That combination of honesty, humor, temptation, and uncertainty gives the song a personality that listeners can easily recognize.

Stapleton’s vocal delivery adds another layer.

His performance brings a mixture of confidence and restraint, allowing the lyrics to carry much of the emotional weight.

A Song That Continued to Grow

The success of “You Should Probably Leave” did not happen overnight.

Its story is more accurately described as a gradual rise.

The song existed for years before release. It became part of an album before being selected as a later single. It then developed into a major song in Stapleton’s catalog and eventually earned Grammy recognition.

That progression is interesting because it challenges the idea that every successful song has to make an immediate impact.

Some recordings take time to find their audience.

Sometimes a song written in one period of an artist’s life becomes even more relevant years later.

Stapleton’s recording demonstrates how patience can sometimes work in a songwriter’s favor.

The Bigger Success of Starting Over

“You Should Probably Leave” was not the only successful part of Starting Over.

The album itself became one of the defining projects of Stapleton’s career.

The record continued the musical direction established by his earlier work while introducing songs that connected strongly with country audiences.

It also helped reinforce Stapleton’s reputation as an artist capable of combining traditional country influences with blues, rock, soul, and roots music.

The album’s success provided the environment in which “You Should Probably Leave” could eventually develop into a standout track.

Why the Song’s Long Journey Matters

The seven-year gap between writing and release is perhaps the most memorable part of the story.

In today’s music industry, listeners are accustomed to rapid release schedules. Songs can be written, recorded, promoted, and released within a relatively short period.

Stapleton’s experience shows another path.

A song can exist quietly for years before reaching the public at the right moment.

That makes the early 2014 performance especially interesting in retrospect.

At the time, nobody could know how far the song would eventually travel.

There was no guarantee that it would become a major single or receive a Grammy.

It was simply a song being performed in Nashville.

Years later, that early performance became part of the song’s history.

A Defining Song in Stapleton’s Catalog

Chris Stapleton has recorded many memorable songs throughout his career, but “You Should Probably Leave” has developed into one of the recordings most closely associated with his modern success.

Its combination of strong songwriting, a distinctive vocal performance, and a relatable story helped it stand out.

The song also demonstrates the value of Stapleton’s approach to music.

He does not need to rely solely on trends.

Instead, his recordings often draw on established country, blues, and roots traditions while still sounding contemporary.

That balance has allowed his music to reach both traditional country listeners and people who may come to his music from other genres.

From a Nashville Stage to a Grammy

The journey of “You Should Probably Leave” can almost be viewed as a timeline of Stapleton’s career.

It began with songwriting in 2014.

An early Nashville performance followed.

Years later, the song appeared on Starting Over.

It was eventually released as the album’s third single.

Then came widespread recognition, chart success, and a Grammy Award in 2022.

The song’s story illustrates how unpredictable the life of a recording can be.

A song that waits years for its opportunity can eventually become one of an artist’s most recognizable works.

A Lasting Example of Patient Songwriting

The continued attention surrounding “You Should Probably Leave” is a reminder that great songs do not always follow a predictable timeline.

Stapleton and his co-writers created the song in 2014, but listeners would have to wait years before hearing the version that eventually became widely known.

That patience ultimately became part of the story.

The song’s success, Grammy recognition, and place within Starting Over show that a recording can continue gaining importance long after the original writing session.

For Chris Stapleton, it is another example of how strong songwriting can survive the passage of time.

What began as a song written with Ashley Gorley and Chris DuBois became a major recording years later and earned one of the industry’s most respected awards.

And perhaps that is what makes the story so compelling.

The song did not need to arrive first.

It simply needed to arrive at the right time.