50 Best Country Songs About Prison

Gritty Tales of Lockup In Country Music

There’s a certain weight that hits when you dive into prison songs in country music. Not just sorrow or regret but a strange mix of reckoning and restless energy. Some tracks are literal, telling stories from behind bars. Others sneak in the theme without naming the bars, carrying that same feeling of being trapped, caught, or running out of time. You might hear a guitar strum that bends the shoulders or a voice that scratches the surface of anger and longing. It hits in the gut in a way pop, rock, country, and R&B songs often try to do, but with grit tuned to a southern twang.

Listening to these tracks isn’t glamorous. There’s sweat and heat, a scrape of boots on concrete, the tension of walls closing in while life moves outside. It’s regret, stubbornness, love lost, and schemes gone sideways. Some voices sound defiant, others crushed under the weight of their choices. Sometimes a line will surprise you with humor or irony in the middle of heavy truth. The songs linger, letting you sit with the mess of being human and contained, which feels oddly freeing.

Not every song fits neatly into a story of cells and bars, but the ones that capture that tension hit hard. They carry anger, longing, escape, and reflection in ways that can make a dusty bar feel like the world outside or a long highway feel like confinement. These songs pull on the threads of human experience tied to consequences and confinement, and some even sneak in subtle nods to redemption or regret. Here are the best country songs about prison that capture all of that weight and mood.

1. 'Folsom Prison Blues' by Johnny Cash

2. 'Mama Tried' by Merle Haggard

3. 'I Got Stripes' by Johnny Cash

4. 'Death Row' by Chris Stapleton

5. 'A Week in a Country Jail' by Tom T. Hall

6. 'The Prisoner's Song' by Hank Snow

7. 'Ol' Red' by Blake Shelton

8. 'San Quentin' by Johnny Cash

9. 'Sing Me Back Home' by Merle Haggard

10. 'Chain Gang' by Sam Cooke

11. 'I'm the Only Hell My Mama Ever Raised' by Johnny Paycheck

12. 'There Ain't No Good Chain Gang' by Johnny Cash and Waylon Jennings

13. 'A Boy Named Sue' by Johnny Cash

14. 'The Long Black Veil' by Lefty Frizzell

15. 'Will You Visit Me on Sundays?' by Merle Haggard

16. 'Wait in the Truck' by Hardy and Lainey Wilson

17. 'High Cost of Living' by Jamey Johnson

18. 'I'd Go to Jail' by Dean Brody

19. 'Behind Bars' by Jelly Roll with Brantley Gilbert and Struggle Jennings

20. 'Wichita Jail' by The Charlie Daniels Band

21. '11 Months and 29 Days' by Johnny Paycheck

22. 'Starkville City Jail' by Johnny Cash

23. 'Christmas in Prison' by John Prine

24. 'I Washed My Hands in Muddy Water' by Stonewall Jackson

25. 'Still Doin' Time' by George Jones

26. 'Bobby' by Reba McEntire

27. 'The Convict and the Rose' by Porter Wagoner

28. 'On the Inside' by Lynne Hamilton

29. 'Chain Gang' by Johnny Cash

30. 'I Went to College, I Went to Jail' by ERNEST and Jelly Roll

31. 'Penitentiary Blues' by David Allan Coe

32. 'Lightning' by Eric Church

33. 'Billy Austin' by Steve Earle

34. 'The Chair' by Marty Robbins

35. 'The Wall' by Freddie Hart

36. 'Roane County Prison' by Bill Monroe

37. 'Boston Jail' by Porter Wagoner

38. 'Chains' by Patty Loveless

39. 'Blackjack County Chain' by Willie Nelson

40. 'Guilty As Can Be' by Cody Johnson

41. 'Stone Walls and Steel Bars' by The Stanley Brothers

42. 'The Sweetest Gift' by The Judds

43. 'Prison to Heaven' by The Avett Brothers

44. 'Whiskey Bent and Jail Bound' by Casper McWade

45. 'Life in Prison' by Merle Haggard

46. 'Women's Prison' by Nicki Bluhm

47. 'In the Jailhouse Now' by Jimmie Rodgers

48. 'The Midnight Special' by Creedence Clearwater Revival

49. 'Ellis Unit One' by Steve Earle

50. 'Stone Hotel' by Jaime Wyatt