Stapleton originally recorded "You Should Probably Leave" for a previous album. The record got canned after its lead single, "What Are You Listening To
," did not perform as expected.
It was actually Stapleton's wife and backing singer Morgane that persuaded him to include the song on Starting Over
. She told him it was time for "You Should Probably Leave" to be officially released into the world, having garnered a following on YouTube.