[7] In August 2006 Crosby performed at the Edinburgh Festival Fringe in two shows: the Comedy Bucket,[8] a stand-up showcase, and Pappy's Fun Club.

As part of Pappy's Fun Club, Crosby returned to the Edinburgh Fringe with Funergy in 2008,[10] World Record Attempt: 200 Sketches in an Hour in 2009,[11] All Business in 2010,[12] and Last Show Ever in 2012.

[15] Crosby took his debut solo stand-up show, Adventure Party, to the Edinburgh Festival Fringe in 2011, where it received a number of 4* reviews.

[19] He co-devised and co-wrote the comedy panel show Hypothetical for UK TV channel Dave.

[20] In June 2019, Crosby launched a new Sunday morning show on Radio X with fellow comedian, Ed Gamble.