In College he started taking song writing seriously. More than just a catchy tune, Josh Wilson tried hard to write clever and original lyrics. He released 2 independent albums while in college. He graduated from Belmont University in 2006, and was soon signed by Sparrow Records.

His debut album entitled Trying to Fit the Ocean In a Cup was released in April 2008 and featured the single 3 Minute Song. Sinse his debut he has released 3 other albums; Life is Not a Snapshot (2009), Josh Wilson (2010), See You (2010).

In 2010 during security delays at Neward Liberty International Airport, Wilson decided to pull out his guitar and entertain his fellow passengers. He played “Hey Jude” and the crowd sang along. Video of the incident was posted multiple times on YouTube and it went viral shortly after.