Discovering John Prine

I am embarassed and ashamed that somehow I had never heard of one the music's most talented songwriters and folk singers. How did I miss this man when he was alive?

I was scrolling through my Instagram feed when I came across actress Rita Wilson singing the prettiest song I had ever heard -- never heard it before. I discovered it was a John Prine song, Summer’s End - she was singing it in honoring him after his death from complications from Covid-19. It was April 20, 2020 and I had never heard of him before, but that song—those lyrics—stopped me in my tracks. As I listened to her sing it a vivid picture of summer and the longing for summer, and I found myself wondering, How have I never listened to this song before? Who is John Prine?

That sent me down the rabbit hole. I started listening to his albums, watching YouTube videos, and before I knew it, I had fallen in love with his music. Prine was more than just a singer-songwriter—he was a storyteller, a humorist, and a poet of everyday life. He wrote songs about people you felt like you knew, or maybe even were.

His music is a mix of humor, heartbreak, and wisdom. Some songs make you laugh, some make you cry, and some do both at the same time.I hope these songs introduce you to his world in the way they did for me and if you already know Prine - I hope you enjoy my quick playlist.

1. I Remember Everything – A Beautiful Farewell

This was the last song Prine ever recorded, and it’s one of his most poignant. It’s soft, reflective, and full of nostalgia—almost like a letter to the past. The way he delivers it, fragile but warm, makes you appreciate the memories we hold onto, even the ones that hurt.

2. Angel from Montgomery – Writing from a Woman’s Perspective

Not many male songwriters write from a woman’s perspective, but Prine did—and he did it brilliantly. This song, about a middle-aged woman looking back on her life, is filled with longing and quiet resignation. The line “Just give me one thing that I can hold on to” is heartbreaking, and Bonnie Raitt’s cover made it a classic.

Here's the Bonnie Raitt version that you may be more familiar with...

3. Sam Stone – The Power of Storytelling

Few songs hit as hard as Sam Stone. It tells the story of a veteran who comes home from war, only to fall into addiction. The imagery is gut-wrenching—"There’s a hole in daddy’s arm where all the money goes". Prine didn’t just write about war—he wrote about what happens after, when the battles follow soldiers home. It’s devastating but necessary.

4. Hello in There – The Loneliness of Aging

This might be one of Prine’s most heartbreaking songs. It’s about the quiet loneliness of old age, when the world moves on and people stop noticing you. “Old people just grow lonesome, waiting for someone to say 'Hello in there, hello’”—that line alone says it all. It’s a reminder to slow down, to check in on people, and to simply see them.

5. Dear Abby – Humor in Music Done Right

Humor in music is rare, but Prine did it effortlessly. Dear Abby is a hilarious take on advice columns, with people writing in about their ridiculous problems—only to be told, “You are what you are and you ain’t what you ain’t.” It’s fun, clever, and impossible not to sing along to.

6. Egg & Daughter Night, Lincoln Nebraska, 1967 (Crazy Bone) – Nostalgia with a Smile

This one is pure Prine—funny, a little strange, and completely charming. It’s a song about small-town traditions, youthful antics, and that one friend who’s just a little bit offbeat. Beneath the humor, there’s a deep appreciation for the weird and wonderful parts of life.

7. The Lonesome Friends of Science – Feeling Out of Place in the World

The feature video at the start of this article is John Prine at his best—blending humor, philosophy, and a bit of existential pondering. He takes the demotion of Pluto and turns it into a bigger reflection on feeling out of step with the world. “I live down deep inside my head”—who hasn’t felt that way at some point? It’s witty, sharp, and somehow both playful and profound. It's definitely one of my favorites of his.

Why John Prine’s Music Sticks with You

John Prine wrote songs that felt real. He could make you laugh in one verse and break your heart in the next. His characters were people you’ve met, or maybe even are. He had this rare ability to find poetry in the every day, making the ordinary feel extraordinary.

The House of Strombo Session – The Perfect Introduction to John Prine

If you really want to experience John Prine, this is the video to watch. The House of Strombo session is one of his best live performances—intimate, warm, and full of his signature storytelling. Between songs, he shares little anecdotes that make you feel like you're right there in the room with him. Whether you're discovering Prine for the first time or revisiting his music, this is 40 minutes well spent.

If you’ve never listened to Prine before, I hope these songs give you a good start. And if you’re already a fan, what are your favorite songs? I’d love to hear them. Let me know in the comments!