John Flynn began writing songs professionally after graduating from Temple University in the 1980. He had intended to study law but a brief sojourn to Nashville’s Music Row led to a publishing contract with Combine Music and a Billboard Magazine Top Forty country recording of his song Rainbows and Butterflies by Billy Swan. Although to this day other country singers continue to cover John’s music, he is most proud of the cut of his song “Old Paint” by recently departed rodeo champion and Capital recording artist Chris Ledoux.

Flynn strayed from country music in the 90’s. His songwriting broadened, as it grew more assured and introspective. He supported his family by working the cover-bar circuit around his hometown of Philadelphia. His self-released CDs From the Hard Box of Time and Haunted By the Ghost of a Chance began to be receive airplay by AAA radio giant WXPN, and a standing ovation followed his first main stage appearance at the 1995 Philadelphia Folk Festival, cemented John’s growing reputation as a dynamic and original contemporary folk artist.

During these years, songs John wrote for his four children became the basis of two highly acclaimed family CDs, Love Takes a Whole Box of Crayons and A Manatee Sneezed on Me, garnering Flynn repeat appearances on the Peabody Award-winning children’s radio program "Kid’s Corner" and the American Library Association’s Notable Recording Award. A self titled release on Sliced Bread Records was produced by Grammy winner Ben Wisch and yielded John critical acclaim and a national top-fifteen slot on Gavin Magazine’s Americana charts.

Although Flynn has performed throughout the country, he has spent most of his family's growing years close to home, doing family concerts through out the Philadelphia region. During this time John also began performing hugely popular assemblies and creative writing workshops in elementary, middle, and high schools.

Flynn regularly sells out the Philadelphia region’s premier listening rooms, The Tin Angel and The Point, and at the invitation of the Philadelphia Phillies, frequently appeared at Veterans Stadium. In fact, on September 28th, 2003, John had the honor of being the last performer to ever appear at the Vet, which was demolished in 2004. Veterans Stadium is also the setting for "I WILL NOT FEAR [9/17/01]", the studio track and bonus anthem that closes John’s 2001 live release, To the Point. "I WILL NOT FEAR" was inspired by the overwhelming response of 40,000 people to John's rendition of "God Bless America", the week that Major League Baseball resumed play following the terrorist attacks on our nation.