100 Timeless Old Country Songs from Willie, Waylon, Loretta + More!


James Lambert


February 1, 2024


February 1, 2024


February 1, 2024

Forget the autotune for a second and think about that razing twang of a steel guitar underneath a starlit sky. That’s the magic of old country songs – the kind Johnny Cash and Patsy Cline poured their hearts into. Certainly, the pop anthems have a place, too, but these classics offer something different: a connection to something real and timeless.

And it’s not all about nostalgia — though, who can resist belting out “Jolene” with friends around a campfire? From Cline’s gut-wrenching ballads to Cash’s outlaw anthems, the songs all explore universal themes: love, loss, struggle, and hope. They paint vivid pictures of small-town America, with the dustbowl grit and twinkle-eyed resilience that echo through the generations.

And the music? Simple, yes, but that’s where the beauty is. Catchy melody, lyrical harmonica, and cracking voice – this can unite people in their minds. And yet, those songs don’t sugar-coat anything; instead, they wear their hearts on their sleeves, touching on life’s ups and downs with a candor that endures even after the last note has faded.

So, while even pop music brings its energy and flavor of a totally different kind of richness of country pop, there’s something to the wellspring of old country music: a timeless legacy, a relatable story, and a feeling that transcends age and trends. It’s a reminder that sometimes, the simplest things can have the most profound impact.

So let’s dive into the lists of the best classic Country Songs of all time. Check them out below and enjoy!

1. Wichita Lineman – Glen Campbell

2. Coat Of Many Colours – Dolly Parton

3. That’s How I Got To Memphis – Tom T. Hall

4. Take Me Home, Country Roads – John Denver

5. Mammas Don’t Let Your Babies Grow Up To Be Cowboys – Waylon Jennings & Willie Nelson

6. Check Yes Or No – George Strait

7. Louisiana Woman, Mississippi Man – Conway Twitty & Loretta Lynn

8. American Remains – The Highwaymen (Feat. Willie Nelson, Johnny Cash, Waylon Jennings, Kris Kristofferson)

9. I Walk The Line – Johnny Cash (With Tennessee Two)

10. Poncho & Lefty – Townes Van Zandt

11. Tennessee Whiskey – George Jones

12. Mama Tried – Merle Haggard

13. Can The Circle Be Unbroken – The Carter Family

14. Take This Job And Shove It – Johnny Paycheck

15. Fast As You – Dwight Yoakam

16. Highwayman – The Highwaymen (Feat. Willie Nelson, Johnny Cash, Waylon Jennings, Kris Kristofferson)

17. Cowpoke – Eddy Arnold

18. Harper Valley P.T.A – Jeannie C. Riley

19. Chattahoochee – Alan Jackson

20. Is Anybody Goin’ To San Antone – Charley Pride

21. Rose Garden – Lynn Anderson

22. The Most Beautiful Girl – Charlie Rich

23. I Wouldn’t Have Missed It For The World – Ronnie Milsap

24. Stand By Your Man – Tammy Wynette

25. Long Haired Country Boy – The Charlie Daniels Band

26. Boulder To Birmingham – Emmylou Harris

27. I’m In A Hurry (And Don’t Know Why) – Alabama

28. God Bless The U.S.A – Lee Greenwood

29. A Country Boy Can Survive – Hank Williams Jr.

30. Go Rest High On That Mountain – Vince Gill

31. Delta Dawn – Tanya Tucker

32. The Gambler – Kenny Rogers

33. Act Naturally – Buck Owens

34. It Must Be Love – Don Williams

35. Fishin’ In The Dark – Nitty Gritty Dirt Band

36. I Love A Rainy Night – Eddie Rabbit

37. Ode To Billie Joe – Bobbie Gentry

38. ’57 Chevrolet – Billie Jo Spears

39. Color Him Father – Linda Martell

40. Why You Been Gone So Long – Jessi Colter

41. Love Hurts – Gram Parsons

42. Old Five And Dimers Like Me – Billy Joe Shaver

43. Sold American – Kinky Friedman

44. The Carroll Country Accident – Porter Wagoner

45. The Brand New Tennessee Waltz – Jesse Winchester

46. Pissin’ In The Wind – Jerry Jeff Walker

47. Longhaired Redneck – David Allan Coe

48. New Cut Road – Guy Clark

49. Amarillo Highway (For Dave Hickey) – Terry Allen

50. Lovin’ Her Was Easier (Than Anything I’ll Ever So Again) – Tompall & The Glaser Brothers

51. Walking The Floor Over You – Ernest Tubb

52. Saginaw, Michigan – Lefty Frizzell

53. Waterloo – Stonewall Jackson

54. She Got The Goldmine (I Got The Shaft) – Jerry Reed

55. If It Ain’t Love (Let’s Leave It Alone) – Connie Smith

56. May The Bird Of Paradise Fly Up Your Nose – Little Jimmy Dickens

57. The Battle Of New Orleans – Johnny Horton

58. Big Iron – Marty Robbins

59. Skip A Rope – Henson Cargill

60. Hello Mary Lou – The Startler Brothers

61. Highway 40 Blues – Ricky Skaggs

62. Leaving Louisiana In The Broad Daylight – The Oak Ridge Boys

63. My Heart Skips A Beat – Buck Owens

64. Don’t It Make My Brown Eyes Blue – Crystal Gayle

65. Islands In The Stream – Dolly Parton & Kenny Rogers

66. King Of The Road – Roger Miller

67. Tulsa Time – Don Williams

68. All The Gold In California – Larry Gatlin & The Gatlin Brothers

69. The Last Thing On My Mind – Porter Wagoner & Dolly Parton

70. Six Days On The Road – Dave Dudley

71. Two More Bottles Of Wine – Emmylou Harris

72. Let Your Love Flow – The Bellamy Brothers

73. Marie Laveau – Bobby Bare

74. Misty – Ray Stevens

75. There Stands The Glass – Webb Pierce

76. Chattanoogie Shoe Shine Boy – Red Foley

77. Old Hippie – The Bellamy Brothers

78. Waltz Across Texas – Ernest Tubb

79. Sunday In The South – Shenandoah

80. Stop And Smell The Roses – Mac Davis

81. Tennessee Flat Top Box – Rosanne Cash

82. Big Bad John – Jimmy Dean

83. I’m Just An Old Chunk Of Coal (But I’m Gonna Be A Diamond Some Day) – John Anderson

84. 16th Avenue – Lacy J. Dalton

85. You Never Even Called Me By My Name – David Allan Coe

86. East Bound And Down – Jerry Reed

87. Convoy – C.W. McCall

88. For The Good Times – Ray Price

89. Should’ve Been A Cowboy – Toby Keith

90. Sold (The Grundy Country Auction Incident) – John Michael Montgomery

91. Dust On The Bottle – David Lee Murphy

92. Bubba Shot The Jukebox – Mark Chesnutt

93. Luckenbach, Texas (Back To The Basics Of Love) – Waylon Jennings (Feat. Willie Nelson)

94. Jambalaya (On The Bayou) – Hank Williams (Feat. Drifting Cowboys)

95. Me And Bobby McGee – Kris Kristofferson

96. Hello Darlin’ – Conway Twitty

97. Jackson – Johnny Cash (With June Carter Cash)

98. It Wasn’t Gods Who Made Honky Tonk Angels – Kitty Wells

99. Amarillo By Morning – George Strait

100. Okie From Muskogee – Merle Haggard


conway twitty, Dolly Parton, George Jones, George Strait, glen campbell, John Denver, Johnny Cash, kris kristofferson, Loretta Lynn, merle haggard, Tom T. Hall, Townes Van Zandt, Waylon Jennings, Willie Nelson



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