Flanagan has performed at the Edinburgh Fringe and toured Britain with stand-up shows. Flanagan became a professional comedian in 1997 after attending a comedy course at Jacksons Lane in 1996. In 2001 he performed in the Big Value Comedy Show at the Edinburgh Fringe as one of four headline acts, and in 2003 co-headlined a show with Nina Conti.[6] He performed his first full-length solo show, What Chance Change? in 2006, and in 2007 was nominated for Best Newcomer at the Edinburgh Comedy Awards. He is touring Britain with The Out Out Tour in 2010/2011.