The 100 Best Americana Songs of All Time (Part 3)
In Part 1, we laid the foundation. In Part 2, we met the outlaws and the poets. Now, in Part 3, we get to the point where the sound gets louder, the edges get rougher, and the definition of “Americana” starts to fray in the best possible way.
This is the era of bar-band sweat, punk-rock attitude, and the 90s/00s revival that proved Americana wasn’t a museum piece—it was a living, breathing, and often screaming thing.
These are the songs that took the storytelling of their heroes and plugged it into a Marshall stack — the kind of spirit NYC Americana bands like Wonderlicks live and breathe.
If you’ve got a favorite that belongs here, let us know in the comments.
21. Steve Earle - “Copperhead Road” (1988)
Why it’s one of the best: This song is a Molotov cocktail of country, folk, and rock and roll. It’s a multi-generational story of rebellion, from moonshining to marijuana farming, all set to a relentless, stomping beat. Earle doesn’t just tell a story; he builds a world. You can feel the mud, the sweat, and the defiance. It’s a song that proved Americana could be both literary and loud, and it kicked the door open for a whole new generation of artists.
22. Jason Isbell - “Cover Me Up” (2013)
Why it’s one of the best: Raw, unflinching, and deeply personal, “Cover Me Up” is a modern masterpiece of confessional songwriting. Isbell lays his struggles with addiction and his journey to sobriety bare, but the song is ultimately a testament to the redemptive power of love. It’s a song that doesn’t just ask for love, but earns it. The raw emotion in his voice, combined with the sparse, powerful arrangement, makes this a song that will be remembered for decades to come.
23. The Jayhawks - “Blue” (1995)
Why it’s one of the best: This song is pure, shimmering melancholy. The harmonies are so tight and beautiful they almost hurt. It’s a song that captures the feeling of being lost in a memory, of a love that’s gone but still feels present. The Jayhawks took the country-rock foundation of bands like The Byrds and Gram Parsons and polished it to a high shine, creating a sound that was both timeless and new. “Blue” is their crowning achievement.
24. Drive-By Truckers - “Decoration Day” (2003)
Why it’s one of the best: This is Southern Gothic storytelling at its finest. A dark, sprawling tale of a family feud, passed down through generations, that feels both epic and tragically intimate. The guitars are loud and angry, but the lyrics are what cut deepest. It’s a song that understands that history isn’t something you read in a book; it’s something you live with, and sometimes die for. It’s a perfect example of how Americana can be both literary and visceral.
25. Gillian Welch - “Orphan Girl” (1996)
Why it’s one of the best: In a world of loud guitars and big productions, Gillian Welch and David Rawlings proved that two voices and two acoustic instruments could be just as powerful. “Orphan Girl” is a song that sounds like it could have been written a hundred years ago, yet it feels completely timeless. It’s a simple, heartbreaking plea for a home, for a place to belong. It’s a reminder that the quietest songs are often the ones that speak the loudest.
26. Ryan Adams - “Come Pick Me Up” (2000)
Why it’s one of the best: This is a song for anyone who has ever been so heartbroken they just wanted to be broken a little bit more. It’s a beautiful, messy, self-destructive anthem. The harmonica wails, the lyrics are full of spite and longing, and the whole thing feels like it’s about to fall apart at any moment. It’s a perfect snapshot of a certain kind of youthful heartbreak, and it’s a song that has been screamed along to by countless people in countless bars for a reason.
27. The Avett Brothers - “I and Love and You” (2009)
Why it’s one of the best: This is a song about leaving. Leaving a city, leaving a relationship, leaving a part of yourself behind. It’s a song that is both grand and intimate, with a soaring chorus that feels like a declaration and verses that feel like a whispered confession. The Avett Brothers brought a punk-rock energy to folk music, and this song is the perfect example of their ability to blend raw emotion with beautiful melodies.
28. Old Crow Medicine Show - “Wagon Wheel” (2004)
Why it’s one of the best: It’s impossible to talk about modern Americana without talking about “Wagon Wheel.” Based on a fragment of a Bob Dylan song, Old Crow Medicine Show created a modern folk classic that has been sung around campfires and in bars all over the world. It’s a song about the simple joy of heading home, and its infectious energy is impossible to resist. It’s a song that has brought countless people into the world of Americana, and for that, it deserves a spot on this list.
29. Whiskeytown - “16 Days” (1997)
Why it’s one of the best: Before Ryan Adams was a solo star, he was the frontman of Whiskeytown, one of the most important bands of the 90s alt-country scene. “16 Days” is a perfect slice of their sound: a ragged, booze-soaked, and utterly brilliant song about being on the road and missing someone. It’s a song that sounds like it was recorded in a single take at 3 AM, and that’s what makes it so special. It’s the sound of a band on the verge of greatness, and the sound of a heart breaking in real time.
30. My Morning Jacket - “The Way That He Sings” (2001)
Why it’s one of the best: This is where Americana gets weird, in the best possible way. My Morning Jacket took the sounds of country and rock and blasted them into outer space with reverb and echo. “The Way That He Sings” is a song that is both beautiful and strange, with a soaring melody and a sense of cosmic wonder. It’s a song that proved that Americana could be more than just stories about dirt roads and pickup trucks; it could be about the mysteries of the universe, too.
These songs prove that Americana is not a static genre.
It’s a conversation, a living tradition that is constantly evolving.
In Part 4, we’ll explore the modern voices who are taking that tradition and pushing it in new and exciting directions.