(Editor's note: This article first appeared in our Winter 2013 edition.)

By John Chambless

Staff Writer

"I wish I could write a little postcard and send it to myself 30 years ago, telling myself all the things I'm going to get to do," John Flynn said with a grin. "It's been an amazing gift to go some of the places that I go. I've been to places I never would have imagined."

At 56, Flynn is a singer-songwriter who's completely content where he is. Living in northern Delaware on a tree-lined street, he has a rich collection of critically acclaimed albums, an evergreen catalog of boisterous children's songs, and a roster of friends that any musician would envy.

Sitting in his living room last month with a mug of black coffee, Flynn was happy to discuss where he's been and where he's going. But first, some history.

In Flynn's den, there's a wall packed with concert posters and memorabilia, photos of him onstage with Kris Kristofferson and Willie Nelson, backstage with Bruce Springsteen, singing the National Anthem at Vet Stadium, and a sepia-toned photo of a dapper man in a suit. It's his grandfather, who ran the Tower Theater in Upper Darby until the late 1960s. So yes, show business is in Flynn's genes.

"He met my grandmother there in the late 1920s when she was singing there," Flynn said. "My grandfather heard her singing, looked out from his office and said, 'That's the woman I'm going to marry.' She was an opera singer. She was the one who told me, when I was very little, that I was supposed to do music."

Flynn was a self-described "straight arrow" as a kid, excelling at Ridley High School and getting two congressional nominations to the U.S. Naval Academy. But he found out that the Navy wouldn't let him bring his guitar to Annapolis, so he changed course. He started writing songs.

He had been playing in bands since high school, working in bars while just slightly underage. Asked if his first band, called Home Free, was any good, Flynn laughed. "No," he said. "It was a little acoustic trio that did America, the Eagles, Fogelberg, that kind of stuff. We were amazed people would come to see us. We got to sing and drink beer and get paid."

Flynn worked in bar bands while attending Temple University, pursuing a degree in political science. But then the music business came calling. He took a job as a staff songwriter at Combine Music in Nashville after he wrote a song called "Rainbows and Butterflies" that was recorded by Billy Swan.

The song was a single for an album that never quite came out, Flynn said. "The publishing company had to decide whether to put the promotional money behind that single, or B.J. Thomas singing 'Hey Won't You Play Another Somebody Done Somebody Wrong Song.' We zoomed up the charts to number 39 and stopped. But I got to see how it all worked. I do get a couple hundred bucks every once in a while from it. It's a little present from the sky."

Riding the 1980s live music boom in Wilmington, when dozens of clubs were booking bands and the Market Street Mall was packed with young adults every weekend night, Flynn had his name everywhere. As disco began to push singer-songwriters out of the way, Flynn decided to make his move to Nashville. "When guys started wearing tights and glitter, I went to country music," he said.

Flynn met his longtime idol, Kris Kristofferson, because Billy Swan was in Kristofferson's band. "Billy used to open the shows on the road," Flynn said. "They were playing together at the Grand Opera House in Wilmington, and I took my parents and met Kris backstage."

Years later, Flynn got a chance to interview Kristofferson for Songwriters Monthly magazine. "I was sitting in a Motel 6 in Nashville and called him," Flynn said. "I over-thought that so much. I wanted to make a good impression, to ask him something he hadn't been asked before. My first question was like 175 words, and it was a yes/no answer," he said, laughing. "It was very humbling to realize that I was out of my depth as an interviewer."

Flynn's friendship with Kristofferson continues to this day, and the star is contributing vocals to an upcoming CD by Flynn titled "Poor Man's Diamonds." It's slated for release this winter.

The current state of country music -- as well as the music business -- is completely out of line with what Flynn grew up with. "Well, Tom Petty said today's country is bad rock and roll played with fiddles," Flynn said. "It gotten to be such a big business that they didn't want to take any chances. ... It's a self-mythologizing feedback loop."

Flynn's songs have always relied on the acoustic roots of folk and country. His original acoustic guitar, with a small hole worn through the wood near the strings, now hangs on his living room wall. After an airline twice misplaced the instrument, Flynn decided it was time to retire it. It's not quite as battered as Willie Nelson's famous acoustic, but it has definitely seen some hard traveling. "It's never sounded better," Flynn said. "It gets better with age."

Apart from Flynn's beautiful songs for adults, there's a catalog of children's music that has made him a star for a whole generation of kids who grew up listening to Kathy O'Connell's "Kids Corner" music hour on WXPN-FM.

Flynn's "The Duck Song" ("If it looks like a duck and it quacks like a duck/And there's duck-do on your pick-up truck/Buddy you can bet your bottom buck/It ain't no armadillo") and "Road Kill Cafe" ("Just scrape it off the tire and we'll toss it on the fire/Come chew the fat at the Road Kill Cafe") made him a superstar for the under-12 set. Today, Flynn said, young adults come to his shows and know every word. "They grew up with those songs and then they made the transition to my other music. I was lucky that they never got embarrassed that they liked me," he said.

The boom in children's music coincided with the childhood of Flynn's own four kids, who are now 17 to 26 years old and involved in music themselves. "The songs came very organically from having little children," he said. "That gave me access to an energy or silliness that opened doors for me as a songwriter. They would write poems and I would try to involve them in the writing process, and show them how that could turn into songs."

By the late 1990s, Flynn felt locked into the children's genre, so he distanced himself from it to focus on his adult songs. He still plays occasional school concerts, where he encourages young people to overcome their fears and write their own music.

"I do a little skit about learning to play the harmonica," he said. "I tell them that since I didn't know anybody else's songs, I made up my own, because you can't do that wrong. Then I blow really hard on the harmonica for about 20 seconds, in an irritating way, to make grown-ups cringe. Kids love this. When the teachers come back and say that the next week there were 15 kids with harmonicas out on the playground, that just makes my day."

Flynn cut back his touring to see his kids grow up, but now that they're older, he's doing more live shows -- on his own terms. One of his highest profile gigs was the 2005 "Train to New Orleans" tour with Arlo Guthrie, Ramblin' Jack Elliott and Willie Nelson, which ended in New Orleans following Hurricane Katrina. "It's times like that that I think I might be on the road I'm supposed to be on," Flynn said. "We played separate sets and then converged to play 'Riding on the City of New Orleans.' I just managed to be standing closer to Willie in the pictures than some of the other musicians," he added, laughing.

Recently, he played with America as they performed songs from their debut album.

"I saw them at the Spectrum in the 1970s and saw them doing 'Sister Golden Hair' on that huge stage in front of 20,000 people, and now I just opened for them," Flynn said, shaking his head. "And they were great. I think the people that make it, and stay, are the people that just love making music."

While admitting that "it's easier for younger people to tour" and joking about his age, Flynn said "It's an incredible gift to get to do something that I care so much about. I don't think I should get to complain about some of the more difficult aspects. I think my mental age is about 23 anyway."

Many of Flynn's songs have an edge of seriousness, taking on social causes and injustice and championing the downtrodden with a clear-eyed vision that makes them polished little anthems.

He has been a supporter of Camp Dreamcatcher in Kennett Square for 15 years. He runs annual concerts to raise money for the therapeutic summer camp for young people dealing with HIV/AIDS, so far raising more than $50,000 for the camp. "This is the first generation to come to adulthood with HIV," Flynn said. "It's a wonderful thing. The kids draw so much strength from the ability to share. ... The camp unleashes this amazing energy and joy. That's what you take away when you visit Camp Dreamcatcher."

Flynn wrote "The Web and the Feather" on his latest CD in honor of the camp.

Flynn is also a board member of Pacem in Terris in Delaware. For the past eight years, he has been a counselor for inmates, and now ex-offenders, through the Howard Young Correctional Institution in Wilmington. "It's all ages, maximum security," he said. "We have twice-weekly meetings. It's a support group that was started by the Franciscans." 

The meetings are not about music, but Flynn said he has done a few concerts in the prison's chapel. Mostly, Flynn listens to the men as they reveal their feelings without fear of reprisal. Inspired by the spirit and resilience of the men, he recently wrote "Prison Bible," a powerful song on his latest CD, "The End of the Beginning."

In a recent issue of the Pacem in Terris newsletter, Flynn wrote about his experiences in the prison: "I've learned about resiliency of spirit from men who have refused to give up on the slim but real chance that they can truly author wholly new endings to the final chapters of their own lives, although almost everyone they've ever known has already closed their books."

After so many years as a musician, Flynn can joke that, "All I ever wanted to be was a has-been, but there's something really cool about being a never-was.

"I'm still looking for my big break," he said. "I've never felt like I've reached a plateau. I'm always finding new fans, like we're getting somewhere. I don't know where, but we're getting somewhere."

For more information, visit www.johnflynn.net.