50 Best Country Songs About Screwing Up

Best Country Tracks on Messing Things Up

There’s a certain kind of weight that comes with screwing up. Not the kind that feels cinematic or life-defining, but the quieter sting where you replay the same line over and over in your head. You said the wrong thing, picked the wrong night, left someone standing in the rain. Country songs live in that territory because the genre never shies away from mistakes, the kind that get tangled in regret and stubborn pride. Some of these tracks are blunt confessions, others are sideways glances at moments where someone tried to laugh off the wreckage but failed.

The mess doesn’t always have to be literal. A song might circle around heartbreak, bad timing, or self-sabotage, and even if it wasn’t written as an admission of failure, it lands in that space when you hear it through your own haze. The mood cuts across pop, rock, country, and R&B songs too, so the thread runs wider than any one sound. Sometimes the hook is playful, sometimes it aches, sometimes it does both in the same verse, which is exactly how messing up feels in real life.

Nobody walks away from their mistakes with a clean narrative. The energy is uneven, part confession, part denial, part shrug. These songs lean into that headspace, capturing how ugly and strange regret can sound when turned up loud. Some aren’t technically tied to mistakes at all, but they hold the same crooked spirit. Here are the best country songs on screwing up.

1. 'What Hurts the Most' by Rascal Flatts

2. 'I Told You So' by Randy Travis

3. 'She Wouldn't Be Gone' by Blake Shelton

4. 'Always on My Mind' by Willie Nelson

5. 'Whiskey Lullaby' by Brad Paisley and Alison Krauss

6. 'He Stopped Loving Her Today' by George Jones

7. 'I'd Rather Be a Fool' by John Pardi

8. 'Come Back Song' by Darius Rucker

9. 'Bigger Mistakes' by Mitchell Tenpenny

10. 'The Losing Kind' by Johnny Cash

11. 'Miss Me More' by Kelsea Ballerini

12. 'Mercy' by Brett Young

13. 'Here's a Quarter (Call Someone Who Cares)' by Travis Tritt

14. 'The Truth' by Jason Aldean

15. 'I Don't Wanna Be Your Friend' by Blake Shelton

16. 'Let Her Go' by The Cadillac Three

17. 'You'll Think of Me' by Keith Urban

18. 'Nobody in His Right Mind Would've Left Her' by George Strait

19. 'Whiskey Glasses' by Morgan Wallen

20. 'Break Up in a Small Town' by Sam Hunt

21. 'Flower Shops' by Ernest and Morgan Wallen

22. 'Better Than I Used to Be' by Tim McGraw

23. 'Drunk on a Plane' by Dierks Bentley

24. 'Why' by Jason Aldean

25. 'Last Kiss' by Taylor Swift

26. 'I'm Not the Devil' by Cody Jinks

27. 'Mistakes' by Don Williams

28. 'Regret in the Morning' by Conner Smith

29. 'Hole in the Wall' by Alan Jackson

30. 'Trouble With a Heartbreak' by Jason Aldean

31. 'Just Passing Through' by Jason Aldean

32. 'The Grand Tour' by George Jones

33. 'I Wish I Didn't Know Now' by Toby Keith

34. 'I Let a Damn Good Woman Leave' by Riley Green

35. 'Give It Away' by George Strait

36. 'Austin' by Blake Shelton

37. 'A Guy Walks Into a Bar' by Tyler Farr

38. 'A Little Bitty Tear' by Burl Ives

39. 'Before He Cheats' by Carrie Underwood

40. 'My Give a Damn's Busted' by Jo Dee Messina

41. 'You Look So Good in Love' by George Strait

42. 'Chasin' You' by Morgan Wallen

43. 'If I Ever Get You Back' by Morgan Wallen

44. 'Whiskey, If You Were a Woman' by Highway 101

45. 'The Devil Went Down to Georgia' by The Charlie Daniels Band

46. 'I Can't Make It Alone' by Waylon Jennings

47. 'Right Girl Wrong Time' by Jon Langston

48. 'Friends in Low Places' by Garth Brooks

49. 'Die From a Broken Heart' by Maddie & Tae

50. 'I Will Always Love You' by Dolly Parton