Old Man Joe traces its roots back to the spring of 1999 when a group of people with similar interests got together to play some music.

"Old Man" Joe Squillace was, at the time, a Disc Jockey on KSLU radio on the Saint Louis University Campus. He had heard that his friend and fellow social worker Jenny Wiley was trying to sell tapes of her playing Celtic music to raise money for an internship in Jamaica. The Old Man invited her onto his show to promote her stuff and play live. They decided after the show to get together and simply jam together - bass and fiddle. Joe's roommate, Dan "the Conga man" Grandone had at his disposal various percussion instruments, including a djembe, Caribbean steel drum, and maracas. The three began to play together and pulled some friends in to cover the other various percussion instruments. A friend and OMJ's "#1" fan said to the group quite bluntly, "Why don't you form a band and play at my party next week." They did, and yet knew the missing link was a guitarist.  The Old Man decided to ask another friend, Andrew Rypel, to join. Andrew had been known for playing for the Pope on his visit to St. Louis, and for his incredible guitar playing on hits like "Spruce Moose." A week later, Old Man Joe played all covers at their friend's party to a small crowd and were a "hit."

The band played their first "gig" in April of 1999. It was a benefit show for Amnesty International and Pax Christi. While the band was apart over the summer, the Old Man invited keyboard player Geoff Zimmerman and vocalist Rose Ehresman to play with the band. The band played numerous shows , but entered the transitional phase again with the graduation and departure of lead vocalist Jenny Wiley. Old Man Joe brought on a drummer, friend Brian Weingart, and a mandolin player, Joel Ferber, another social justice freedom fighter. The full band came together again in December 200 to create the following lineup: