The Best Classic Country Songs Playlist

From the 60s to the 90s, this is Holler's Classic Country Songs Playlist. Featured Artist: Merle Haggard & Willie Nelson.

Holler Country Music

From the 60s to the 90s, this is Holler's Classic Country Songs Playlist. Featured Artist: Merle Haggard & Willie Nelson.

November 26, 2021 4:00 am GMT
Last Edited June 29, 2023 12:51 pm GMT

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Where would contemporary country be today without old country songs?

We don't want to even think about it, so instead we're simply going to enjoy five decades of the finest country music to ever be written.

From Waylon to Willie, Dolly to Loretta, this is a who's who of country music Hall of Famers.

See the full tracklist for Holler's Classic Country Songs Playlist below:

  1. 1.

    Wichita Lineman

    Glen Campbell

  2. 2.

    Coat Of Many Colours

    Dolly Parton

  3. 3.

    That's How I Got To Memphis

    Tom T. Hall

  4. 4.

    Take Me Home, Country Roads

    John Denver

  5. 5.

    Mammas Don't Let Your Babies Grow Up To Be Cowboys

    Waylon Jennings & Willie Nelson

  6. 6.

    Check Yes Or No

    George Strait

  7. 7.

    Louisiana Woman, Mississippi Man

    Conway Twitty & Loretta Lynn

  8. 8.

    American Remains (With Willie Nelson, Johnny Cash, Waylon Jennings and Kris Kristofferson)

    The Highwaymen

  9. 9.

    I Walk The Line (With Tennessee Two)

    Johnny Cash

  10. 10.

    Poncho & Lefty

    Townes Van Zandt

  11. 11.

    Tennessee Whiskey

    George Jones

  12. 12.

    Mama Tried

    Merle Haggard

  13. 13.

    Can The Circle Be Unbroken

    The Carter Family

  14. 14.

    Take This Job And Shove It

    Johnny Paycheck

  15. 15.

    Fast As You

    Dwight Yoakam

  16. 16.

    Highwayman (With Willie Nelson, Johnny Cash, Waylon Jennings And Kris Kristofferson)

    The Highwaymen

  17. 17.


    Eddy Arnold

  18. 18.

    Harper Valley P.T.A

    Jeannie C. Riley

  19. 19.


    Alan Jackson

  20. 20.

    Is Anybody Goin' To San Antone

    Charley Pride

  21. 21.

    Rose Garden

    Lynn Anderson

  22. 22.

    The Most Beautiful Girl

    Charlie Rich

  23. 23.

    I Wouldn't Have Missed It For The World

    Ronnie Milsap

  24. 24.

    Stand By Your Man

    Tammy Wynette

  25. 25.

    Long Haired Country Boy

    The Charlie Daniels Band

  26. 26.

    Boulder To Birmingham

    Emmylou Harris

  27. 27.

    I'm In A Hurry (And Don't Know Why)


  28. 28.

    God Bless The U.S.A

    Lee Greenwood

  29. 29.

    A Country Boy Can Survive

    Hank Williams Jr.

  30. 30.

    Go Rest High On That Mountain

    Vince Gill

  31. 31.

    Delta Dawn

    Tanya Tucker

  32. 32.

    The Gambler

    Kenny Rogers

  33. 33.

    Act Naturally

    Buck Owens

  34. 34.

    It Must Be Love

    Don Williams

  35. 35.

    Fishin' In The Dark

    Nitty Gritty Dirt Band

  36. 36.

    I Love A Rainy Night

    Eddie Rabbit

  37. 37.

    Ode To Billie Joe

    Bobbie Gentry

  38. 38.

    '57 Chevrolet

    Billie Jo Spears

  39. 39.

    Color Him Father

    Linda Martell

  40. 40.

    Why You Been Gone So Long

    Jessi Colter

  41. 41.

    Love Hurts

    Gram Parsons

  42. 42.

    Old Five And Dimers Like Me

    Billy Joe Shaver

  43. 43.

    Sold American

    Kinky Friedman

  44. 44.

    The Carroll Country Accident

    Porter Wagoner

  45. 45.

    The Brand New Tennessee Waltz

    Jesse Winchester

  46. 46.

    Pissin' In The Wind

    Jerry Jeff Walker

  47. 47.

    Longhaired Redneck

    David Allan Coe

  48. 48.

    New Cut Road

    Guy Clark

  49. 49.

    Amarillo Highway (For Dave Hickey)

    Terry Allen

  50. 50.

    Lovin' Her Was Easier (Than Anything I'll Ever So Again)

    Tompall & The Glaser Brothers

  51. 51.

    Walking The Floor Over You

    Ernest Tubb

  52. 52.

    Saginaw, Michigan

    Lefty Frizzell

  53. 53.


    Stonewall Jackson

  54. 54.

    She Got The Goldmine (I Got The Shaft)

    Jerry Reed

  55. 55.

    If It Ain't Love (Let's Leave It Alone)

    Connie Smith

  56. 56.

    May The Bird Of Paradise Fly Up Your Nose

    Little Jimmy Dickens

  57. 57.

    The Battle Of New Orleans

    Johnny Horton

  58. 58.

    Big Iron

    Marty Robbins

  59. 59.

    Skip A Rope

    Henson Cargill

  60. 60.

    Hello Mary Lou

    The Startler Brothers

  61. 61.

    Highway 40 Blues

    Ricky Skaggs

  62. 62.

    Leaving Louisiana In The Broad Daylight

    The Oak Ridge Boys

  63. 63.

    My Heart Skips A Beat

    Buck Owens

  64. 64.

    Don't It Make My Brown Eyes Blue

    Crystal Gayle

  65. 65.

    Islands In The Stream

    Dolly Parton & Kenny Rogers

  66. 66.

    King Of The Road

    Roger Miller

  67. 67.

    Tulsa Time

    Don WIlliams

  68. 68.

    All The Gold In California

    Larry Gatlin & The Gatlin Brothers

  69. 69.

    The Last Thing On My Mind

    Porter Wagoner & Dolly Parton

  70. 70.

    Six Days On The Road

    Dave Dudley

  71. 71.

    Two More Bottles Of Wine

    Emmylou Harris

  72. 72.

    Let Your Love Flow

    The Bellamy Brothers

  73. 73.

    Marie Laveau

    Bobby Bare

  74. 74.


    Ray Stevens

  75. 75.

    There Stands The Glass

    Webb Pierce

  76. 76.

    Chattanoogie Shoe Shine Boy

    Red Foley

  77. 77.

    Old Hippie

    The Bellamy Brothers

  78. 78.

    Waltz Across Texas

    Ernest Tubb

  79. 79.

    Sunday In The South


  80. 80.

    Stop And Smell The Roses

    Mac Davis

  81. 81.

    Tennessee Flat Top Box

    Rosanne Cash

  82. 82.

    Big Bad John

    Jimmy Dean

  83. 83.

    I'm Just An Old Chunk Of Coal (But I'm Gonna Be A Diamond Some Day)

    John Anderson

  84. 84.

    16th Avenue

    Lucy J. Dalton

  85. 85.

    You Never Even Called Me By My Name

    David Allan Coe

  86. 86.

    East Bound And Down

    Jerry Reed

  87. 87.


    C.W. McCall

  88. 88.

    For The Good Times

    Ray Price

  89. 89.

    Should've Been A Cowboy

    Toby Keith

  90. 90.

    Sold (The Grundy Country Auction Incident)

    John Michael Montgomery

  91. 91.

    Dust On The Bottle

    David Lee Murphy

  92. 92.

    Bubba Shot The Jukebox

    Mark Chesnutt

  93. 93.

    Luckenbach, Texas (Back To The Basics Of Love) (Feat. Willie Nelson)

    Waylon Jennings

  94. 94.

    Jambalaya (On The Bayou) (Feat. Drifting Cowboys)

    Hank Williams

  95. 95.

    Me And Bobby McGee

    Kris Kristofferson

  96. 96.

    Hello Darlin'

    Conway Twitty

  97. 97.

    Jackson (With June Carter Cash)

    Johnny Cash

  98. 98.

    It Wasn't Gods Who Made Honky Tonk Angels

    Kitty Wells

  99. 99.

    Amarillo By Morning

    George Strait

  100. 100.

    Okie From Muskogee

    Merle Haggard

Subscribe and listen to Holler's Classic Country Songs Playlist above.

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Written by Jof Owen
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