50 Best Country Songs About Taking Chances
Best Country Songs That Embrace Risk and New Paths
There’s a kind of spark that comes when you decide to roll the dice. It’s not pure courage, not pure recklessness, but something twitchy and alive sitting in between. You catch it in the way a lyric stretches out a moment before it breaks, like standing at the edge of a plan you can’t quite see through. These tracks lean into that nervous charge, that split second before you pick a lane and hope the road takes you somewhere worth it.
The feeling has roots in country storytelling, but you hear it echoed across pop, rock, country, and R&B songs too. Some of the picks here drift outside the literal meaning, yet they carry the same spirit of risk and possibility. They tap into the jittery kind of hope that rides along with fear, where saying yes to something unsteady becomes the only way forward. It’s messy, it’s uneasy, and somehow it’s exactly what makes the music land.
Not every chance comes wrapped in triumph. Some bring heartbreak, some stumble into humor, some pull out a surprise that makes no sense until later. That’s the beauty of these tracks—they hold the tension without smoothing it out. Here are the best country songs that capture the feeling of taking chances.
Top 10 Country Songs About Taking a Chance
1. 'Live Like You Were Dying' by Tim McGraw
2. 'I Hope You Dance' by Lee Ann Womack
3. 'The Gambler' by Kenny Rogers
4. 'Starting Over' by Chris Stapleton
5. 'Take a Chance' by Cody Johnson
6. 'Wide Open Spaces' by Dixie Chicks
7. 'Something Like That' by Tim McGraw
8. 'My Next Thirty Years' by Tim McGraw
9. 'Fast As You' by Dwight Yoakam
10. 'Chance Worth Taking' by Mitchell Tenpenny
Country Music About Taking a Risk #11 to 20
11. 'Take a Little Ride' by Jason Aldean
12. 'Free and Easy Down the Road I Go' by Dierks Bentley
13. 'Runnin' Outta Moonlight' by Randy Houser
14. 'Wagon Wheel' by Old Crow Medicine Show
15. 'The House That Built Me' by Miranda Lambert
16. 'The Climb' by Miley Cyrus
17. 'Ready, Set, Don't Go' by Billy Ray Cyrus
18. 'Fly Over States' by Jason Aldean
19. 'Days Go By' by Keith Urban
20. 'It Won't Be Long' by George Birge
Country Songs on New Beginnings #21 to 30
21. 'Good as I Was to You' by Cody Johnson
22. 'Long Haul' by Ian Munsick
23. 'Something New' by Jake Owen
24. 'Crazy Little Thing Called Love' by Dwight Yoakam
25. 'Godspeed (Sweet Dreams)' by Radney Foster
26. 'When I Get Where I'm Going' by Brad Paisley
27. 'Dirt Road Anthem' by Jason Aldean
28. 'Tough People' by Drew Baldridge
29. 'I'll Be There for You' by The Rembrandts
30. 'Head Over Boots' by Jon Pardi
Country Songs About a Leap of Faith #31 to 40
31. 'Chasin' That Neon Rainbow' by Alan Jackson
32. 'It's a Great Day to Be Alive' by Travis Tritt
33. 'You've Got to Stand for Something' by Aaron Tippin
34. 'I Walk the Line' by Johnny Cash
35. 'God's Gonna Cut You Down' by Johnny Cash
36. 'The Good Stuff' by Kenny Chesney
37. 'Something to Talk About' by Bonnie Raitt
38. 'Man! I Feel Like a Woman!' by Shania Twain
39. 'Before He Cheats' by Carrie Underwood
40. 'Let 'er Rip' by The Chicks
Country Songs About New Chapters #41 to 50
41. 'There Goes My Life' by Kenny Chesney
42. 'You Never Can Tell' by Chuck Berry
43. 'Take It Easy' by Eagles
44. 'Take Me Home, Country Roads' by John Denver
45. 'A Little Bit of Life' by Craig Morgan
46. 'I'm a Survivor' by Reba McEntire
47. 'She's in Love with the Boy' by Trisha Yearwood
48. 'Friends in Low Places' by Garth Brooks
49. 'Humble and Kind' by Tim McGraw
50. 'I Can See Clearly Now' by Johnny Nash
© 2025 Carson McQueen
