- Covered Up: Although Stapleton wrote it, "Either Way" was originally recorded by Lee Ann Womack in 2008.
- His "Tennessee Whiskey" is radically different from either George Jones' or David Allan Coe's versions.
- Signature Song: "Tennessee Whiskey".
- Tear Jerker: "Broken Halos" is a simple yet poignant tribute to those who have died too soon.
- From his time with the Steeldrivers, "Can You Run" has a reputation for bringing out Tears of Joy.I've got to stand up tall before I'm done
Wrap these hands of mine around a gun
Chase the taste of bondage from my tongue
Can you run
Can you run - The lyrics of "Fire Away" are bad enough on their own, with a narrator resigned to the fact that their relationship will never be happy. The music video adds what appears to be borderline or bipolar disorder into the mix.
- From his time with the Steeldrivers, "Can You Run" has a reputation for bringing out Tears of Joy.
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