Stephen Lynch began his career performing his comedy songs at venues around New York City. Caroline's and Catch a Rising Star were two of his regular comedy clubs in the city. He was also on a number of radio shows and became a regular on Opie and Anthony.

Lynch's mix of comedy and music made it possible for him to perform at the House of Blues, The Town Hall and even the Kennedy Center which are geared more toward music than comedy. 

His career took off after his Comedy Central Presents special in 2000.  He also performed on Comedy Central's Premium Blend, The World Comedy Tour, and The World Stands Up. Lynch has opened for comedians Jay Mohr, Jeff Foxworthy, Steven Wright, Robert Francis "Bobcat" Goldthwait, and Lewis Black. Stephen had the title role in the Broadway version of The Wedding Singer.