John Prine is 73 years old and has a career that spanned to almost 50 years. He is a two-time Grammy-winner, singer-songwriter, Bob Dylan and Kris Kristofferson praised him, Bette Midler and Bonnie Raitt recorded his songs but little did people know that he has an inspiring Cinderella-story to tell.

1. John Prine learned the guitar when he was just 14 

He was taught by his brother how to play guitar at age fourteen. He also started writing songs just because he felt it was easier than trying to learn other people’s songs.

“My oldest brother, Dave, taught me three chords on the guitar when I was about 14. He was teaching himself to play fiddle and needed someone to play rhythm for him. I believe I wrote my first songs in that first year after I learned to play,” Prine said.

2. John Prine was called the next Bob Dylan 

Even before John Prine’s debut in 1971, he was already being dubbed as the next Bob Dylan. Dylan himself is a fan, he joined Prine onstage during Prine’s Sept 9, 1972, residency at the Bitter End in NYC. They did three songs together – Sam Stone, Donald & Lydia and Far From Me.

In Dylan’s 2009 interview, he was also all praises on Prine: “Prine’s stuff is pure Proustian existentialism. Midwestern mindtrips to the nth degree. And he writes beautiful songs. I remember when Kris Kristofferson first brought him on the scene. All that stuff about ‘Sam Stone’ the soldier junky daddy and ‘Donald and Lydia,’ where people make love from ten miles away. Nobody but Prine could write like that.”

3. His songs have a story to tell

Prine is full of imagination that his songs have sprung some of the most beloved characters and familiar scenarios. Did you know that his hit-song “Paradise” was a real place? It’s actually the town called Paradise in Muhlenberg County, Kentucky, where the Tennessee Valley Authority operated the Paradise Fossil Plant, a coal-fired electric generating station.

“Paradise was a real place in Kentucky, and while I was in the army in Germany, my father sent me a newspaper article telling me how the coal company had bought the place out,” Prine said.

“It was a real Disney-looking town. It sat on the river, had to general stores, and there was one black man in town, Bubby Short. He looked like Uncle Remus and hung out with my Granddaddy Ham, my mom’s dad, all-day fishing for catfish. Then the bulldozers came in and wiped it all off the map.”

His popular song “Hello in There” also has a story to tell about aging.

”I’ve always had an affinity for old people. I used to help a buddy with his newspaper route, and I delivered to a Baptist old peoples’ home where we’d have to go room-to-room. And some of the patients would kind of pretend that you were a grandchild or nephew that had come to visit, instead of the guy delivering papers. That always stuck in my head,” Prine said.

4. He was one of the first singer/songwriters to start his own label, Oh Boy Records

In 1984, Prine started his own label, Oh Boy Records, together with his manager Al Bunetta and their friend Dan Einstein

“When we started it, it was so unheard of, that people thought I was shooting myself in the foot by turning down major label offers, but I wasn’t. The only thing I did love was going out on the road; I loved playing for people and I loved writing songs, but I didn’t love working,” Prine said.

“Now more than ever, it’s important to know that you own your own stuff. The major labels are basically there for high finance loans—you could go to a bank and do the same thing for less money and put a loan behind your career instead of a major label throwing parties for you and charging you, and giving you the ticket and not asking what you want to eat.”

5. Meeting his wife was love at first sight

John Prine’s wife is Fiona Whelan. “I was at this bar trying to get a drink, and I was 14 people back,” Prine said.

“I had my guitar with me. I couldn’t get to the front, so I went around to the other side. And there was this Irish actress at the end …  And oh yeah, it was love at first sight.” They married in 1996 and had two sons, Tommy and Jack.  Prine also adopted Fiona’s son from a previous marriage, Jody.

6. John Prine released his first-ever songbook, called Beyond Words

In 2017, Prine released his first-ever songbook, called Beyond Words. It has a great overview of Prine’s songs and lyrics.

The book also features photos from every phase of Prine’s life like the information card he filled out to sign up for an open mic at Chicago’s Fifth Peg in 1969, the original handwritten draft of the widely covered “Angel from Montgomery”, and so much more.

“I went through it while we were putting the book together, I went through it one page at a time. And when the book was published and they sent me a copy to look at, the very first time I looked at it, it was really too emotional for me to go through the whole book,” Prine said.

“I never saw all those pictures together, that clear, and in that big space and that’s how personal the pictures were to me just, I had to stop turning the pages for a while and I had to wait a few more weeks before I could actually sit down and enjoy the book.”

7. John Prine net worth is $6 million

According to some sources, Prine’s net worth is said to be $6 million while others believe that he is worth more than 300 million dollars.

8. John Prine battled cancer, twice.

Prine had been through a lot in the past few years. He had neck cancer in early 1998 and lung cancer in 2013. His neck cancer has severed nerves in his tongue and damaged his salivary glands. He underwent surgery, endured six weeks of radiation therapy and spent a year in speech therapy. 

Indeed, singer-songwriter John Prine’s songs have embraced pain with kindness and a wicked and quirky sense of humor.