Friday, November 21, 2025

20th Century Americana: Top 100 Songs

20th Century Americana:

Top 100 Songs

Americana music is a celebration of roots-oriented musical forms that are heavily associated with the United States. It reaches back hundreds of years to traditional music, gospel, Negro spirituals, folk, blues, and country for its influence although it is framed in a more modern context. It really surfaced in the late ‘60s as an outgrown of the folk rock movement with artists like The Band and The Grateful Dead becoming some of the best known groups to incorporate it into their music.

To create this list, 27 lists focused on Americana songs were aggregated alongside lists about folk, folk rock, country, and country rock. Added into the mix were other songs from artists featured on those lists. Those songs appearing on the most lists were then ranked based on their overall status in Dave’s Music Database. This list is focused on Americana music in the 20th century. A separate list has been created that focuses on Americana music in the 21st century.

Click here to see other genre-specific song lists.

1. The Band “The Weight” (1968)
2. The Band (1969), Joan Baez (1971) “The Night They Drove Ol’ Dixie Down”
3. The Band “Up on Cripple Creek” (1969)
4. The Grateful Dead “Truckin’” (1970)
5. The Black Crowes “Hard to Handle” (1990)
6. Bonnie Raitt “Something to Talk About” (1991)
7. The Grateful Dead “Uncle John’s Band” (1970)
8. Neil Young “Harvest Moon” (1992)
9. Steve Earle “Copperhead Road” (1988)
10. Jerry Jeff Walker (1968), The Nitty Gritty Dirt Band (1970) “Mr. Bojangles”

11. The Grateful Dead (1970), Lyle Lovett (1991) “Friend of the Devil
12. The Grateful Dead “A Touch of Grey” (1987)
13. Bonnie Raitt “I Can’t Make You Love Me” (1991)
14. Steve Goodman (1971), Arlo Guthrie (1972), Willie Nelson (1984) “City of New Orleans”
15. Stray Cats “Rock This Town” (1981)
16. Bruce Springsteen “Atlantic City” (1982)
17. John Stewart “Gold” (1979)
18. Lyle Lovett & Randy Newman “You’ve Got a Friend in Me” (1995)
19. Townes Van Zandt (1972), Willie Nelson & Merle Haggard (1983) “Pancho and Lefty”
20. Bonnie Raitt “Love Sneakin’ Up on You” (1994)

21. Bonnie Raitt “Nick of Time” (1989)
22. The Grateful Dead “Sugar Magnolia” (1970)
23. The Black Crowes “Remedy” (1992)
24. The Byrds “Hickory Wind” (1968)
25. Traveling Wilburys “Handle with Care” (1988)
26. Tom Petty “You Don’t Know How It Feels” (1994)
27. Gram Parsons “Return of the Grievous Angel” (1974)
28. Lyle Lovett “If I Had a Boat” (1988)
29. The Nitty Gritty Dirt Band “An American Dream” (1979)
30. The Grateful Dead “Dark Star” (1968)

31. The Flying Burrito Brothers (1969), Emmylou Harris (1975) “Sin City”
32. The Traveling Wilbuys “End of the Line” (1988)
33. The Byrds “You Ain’t Goin’ Nowhere” (1968)
34. Bruce Cockburn “If I Had a Rocket Launcher” (1984)
35. The Black Crowes “Jealous Again” (1990)
36. Bruce Springsteen “The Ghost of Tom Joad” (1995)
37. The Band “Rag Mama Rag” (1969)
38. John Prine (1971), Bonnie Raitt (1971) “Angel from Montgomery”
39. The Black Crowes “She Talks to Angels” (1990)
40. The Grateful Dead “Casey Jones” (1970)

41. Bob Dylan “Mississippi” (1997)
42. Lyle Lovett “She’s No Lady” (1988)
43. Lyle Lovett “Nobody Knows Me” (1989)
44. Lucinda Williams “Car Wheels on a Gravel Road” (1998)
45. The Flying Burrito Brothers “Christine’s Tune (Devil in Disguise)” (1969)
46. Gram Parsons “She” (1973)
47. The Byrds “Ballad of Easy Rider” (1969)
48. Robbie Robertson “Somewhere Down the Crazy River” (1987)
49. The Jayhawks “Blue” (1995)
50. The Byrds “One Hundred Years from Now” (1968)

51. John Hiatt “Have a Little Faith in Me” (1987)
52. Stray Cats “Stray Cat Strut” (1981)
53. Bruce Cockburn “Lovers in a Dangerous Time” (1984)
54. Lyle Lovett “Private Conversation” (1996)
55. The Grateful Dead “Ripple” (1970)
56. The Flying Burito Brothers “Hot Burrito #1” (1969)
57. The Grateful Dead “Box of Rain” (1970)
58. Bruce Springsteen “We Shall Overcome” (1998)
59. Gram Parsons & Emmylou Harris “Love Hurts” (1974)
60. The Band “I Shall Be Released” (1968)

61. Emmylou Harris “Boulder to Birmingham” (1975)
62. Cracker “Teen Angst (What the World Needs Now)” (1992)
63. The Flying Burrito Brothers “Wild Horses” (1970)
64. Dillard & Clark “Train Leaves Here This Morning” (1968)
65. Lyle Lovett “Pontiac” (1988)
66. Bruce Springsteen “Johnny 99” (1982)
67. Billy Bragg & Wilco “California Stars” (1998)
68. Son Volt “Drown” (1996)
69. Little Feat “Willin’” (1978)
70. Lyle Lovett “Step Inside This House” (1998)

71. Lyle Lovett “Give Back My Heart” (1987)
72. The Jayhawks “Waiting for the Sun” (1992)
73. Lyle Lovett “L.A. County” (1988)
74. Lyle Lovett “Cowboy Man” (1986)
75. Lyle Lovett “Here I Am” (1989)
76. Bob Dylan “Everything Is Broken” (1989)
77. The Grateful Dead “Alabama Getaway” (1980)
78. John Hiatt “Memphis in the Meantime” (1987)
79. The Nitty Gritty Dirt Band “Make a Little Magic” (1980)
80. Steve Earle “Guitar Town” (1986)

81. John Prine “Hello in There” (1971)
82. John Hiatt “Drive South” (1988)
83. Stray Cats “She’s Sexy + 17” (1983)
84. The Black Crowes “Thorn in My Pride” (1992)
85. The Byrds “Chestnut Mare” (1970)
86. The Traveling Wilburys “She’s My Baby” (1990)
87. Bonnie Raitt “Love Letter” (1989)
88. John Hiatt “Child of the Wild Blue Yonder” (1990)
89. John Hiatt “Slow Turning” (1988)
90. Gram Parsons “Brass Buttons” (1974)

91. Bonnie Raitt “Thing Called Love” (1989)
92. John Hiatt “Tennessee Plates” (1988)
93. Lyle Lovett “Church” (1992)
94. Robbie Robertson & BoDeans “Showdown at Big Sky” (1987)
95. Lyle Lovett & Keb’ Mo’ “Till It Shines” (1999)
96. Neil Young “Philadelphia” (1994)
97. The Grateful Dead “Dire Wolf” (1970)
98. Bob Dylan “Dignity” (1989)
99. John Stewart “Midnight Wind” (1979)
100. Lyle Lovett “You Can’t Resist It” (1986)


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First posted 11/20/2025; last updated 11/21/2025.

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