The 100 Best Americana Songs of All Time (Part 2)
This is the second part of our Best Americana Songs listings. Part 1 was the foundation. Part 2 is where the music gets its scars.
This is the stretch where “Americana” stops sounding like a genre and starts sounding like a life: the outlaws who refused to play nice, the songwriters who wrote like journalists, and the voices that made hard choices feel holy. If you’ve got a favorite that belongs here (or a song you think I got wrong), tell us in the comments.
11. Waylon Jennings - “Are You Sure Hank Done It This Way” (1975)
Why it’s one of the best: This is a turning-point song that feels like a friendly question and a warning at the same time. Waylon isn’t just name-checking Hank Williams—he’s asking what happens when the business gets bigger than the music, and when the “rules” start choking the people who made the rules worth breaking. It’s tough without being cruel, and it’s proud without turning into a speech. It still sounds like somebody taking a deep breath and choosing the hard road on purpose.
12. Willie Nelson - “Blue Eyes Crying in the Rain” (1975)
Why it’s one of the best: Willie takes an old song and makes it feel like a private thought you weren’t supposed to overhear. Nothing is rushed. The guitar is spare, the vocal is soft, and the heartbreak is the point—not the performance of heartbreak. Americana lives in that kind of restraint: the trust that a simple line, sung honestly, can carry a whole history. It’s a reminder that “big” songs don’t have to be loud.
13. Guy Clark - “Desperados Waiting for a Train” (1975)
Why it’s one of the best: This is songwriting as memory—plainspoken, vivid, and devastating in the quiet way. Guy Clark draws a full person with just a few details: work clothes, old stories, a certain kind of dignity that doesn’t need applause. And by the end, the song has done the sneaky thing great Americana does: it’s not only about “him” anymore. It’s about all the people who raised us, drifted away, or got older right in front of us while we were busy.
14. Kris Kristofferson - “Me and Bobby McGee” (1970)
Why it’s one of the best: Everybody remembers the line about freedom, but the whole song is the point: two people moving through a wide American landscape, living on thin margins, making something like a home out of motion. Kristofferson writes it like a real story—specific places, small moments, and the kind of goodbye that doesn’t come with closure. It’s romantic and worn-out at the same time, which is basically the Americana sweet spot.
15. John Prine - “Angel from Montgomery” (1971)
Why it’s one of the best: John Prine’s gift was empathy without pity, and this song is the clearest proof. He steps into someone else’s life—someone tired, someone stuck, someone still hoping—and he never turns them into a punchline or a symbol. Every line feels lived-in: the kitchen, the weather, the quiet desperation, the small fantasy of being “an angel” just to feel weightless for once. It’s one of those songs that makes you listen more kindly to the world.
16. Townes Van Zandt - “Pancho and Lefty” (1972)
Why it’s one of the best: This is a whole novel in a few minutes, told with the calm confidence of someone who knows the ending and can’t change it. Townes writes like a poet who doesn’t need fancy words—just the right ones. The song is full of dust, friendship, betrayal, and the way legends get built after the real people are gone. You can argue about what it “means,” but you can’t argue with how it feels: like a campfire story that leaves you colder.
17. Gram Parsons - “Return of the Grievous Angel” (1974)
Why it’s one of the best: If Americana has a “heartbreak highway” wing, Gram Parsons helped pave it. This song is tender and messy and beautiful—like love that doesn’t clean up after itself. The melody floats, the mood aches, and the whole thing feels like it’s chasing a person it can’t quite catch. It’s country and rock and gospel-sad all at once, which is exactly why it still belongs in this conversation.
18. Bruce Springsteen - “The River” (1980)
Why it’s one of the best: Springsteen takes big themes—youth, responsibility, regret—and makes them personal enough to hurt. “The River” is about the gap between what you thought your life would be and what it becomes when bills, jobs, and bad timing show up. It’s not hopeless, exactly. It’s just honest. And that honesty—working-class, clear-eyed, still human—is why it sits comfortably in Americana, even if it came out of an arena-rock world.
19. Merle Haggard - “Okie from Muskogee” (1969)
Why it’s one of the best: This one is complicated—and that’s why it matters. It’s a cultural snapshot from a tense moment in America, delivered with Merle’s sharp wit and perfect phrasing. People still debate how literal it is, how much is satire, and what it says about class and identity. But as a piece of Americana, it’s undeniable: a song that captured a real divide, in real time, and never stopped starting arguments.
20. Lucinda Williams - “Drunken Angel” (1998)
Why it’s one of the best: Lucinda can make a portrait with a few brushstrokes, and “Drunken Angel” is one of her most tender. It’s a love song, an elegy, and a hard truth all at once—full of affection, damage, and grace. She doesn’t romanticize the mess, but she doesn’t look away from the person inside it, either. That balance—dirt under the nails, light still getting in—is a big part of what modern Americana is.
That’s the thing about these songs: they don’t feel “old.” They feel lived-in.
They’re about choosing your own rules, telling the truth even when it costs you, and finding beauty in the mess of real life.
In Part 3, we’ll follow the sound as it gets louder and weirder—where Americana collides with punk attitude, bar-band sweat, and the 90s/00s revival that kept this whole tradition moving.