"You Should Probably Leave" is a song by Chris Stapleton, released on May 17, 2021, as the third single from his album "Starting Over." The song tells the story of an on-again, off-again couple who repeatedly come back together despite knowing the relationship won't end well. The lyrics capture the temptation and complexity of this reunion, with the title phrase serving as advice and a refrain throughout the song. The twist in the narrative is that even though the protagonist knows it's best for the other to leave, they end up spending the night together, with emotions reversed by morning. The song blends country with blues and roots elements, reflecting Stapleton's signature style. It was co-written by Stapleton, Ashley Gorley, and Chris DuBois. Interestingly, it is one of Stapleton's older songs, dating back to around 2013 before his major-label breakthrough, but was added to the 2020 album "Starting Over" upon the encouragement of Stapleton's wife, Morgane. Critically acclaimed, "You Should Probably Leave" won the Grammy Award for Best Country Solo Performance in 2022 and achieved significant chart success, including reaching No. 1 on several country charts in the U.S. and Canada. The song is noted for its storytelling, emotional depth, and blending of soulful musical influences with country tradition.