Crosby was originally a teacher but left the profession to try comedy in 2004. He has since performed stand-up and sketch comedy all over the world, and was a semi-finalist for the
BBC New Act 2005. He comperes at several comedy venues including the Horsebridge Comedy Club in Whitstable. Crosby is a founding member of sketch team
Pappy's, formerly known as Pappy's Fun Club. In August 2006 Crosby performed at the
Edinburgh Festival Fringe in two shows: the Comedy Bucket, a stand-up showcase, and Pappy's Fun Club. In August 2007 the Edinburgh run of Pappy's Fun Club was nominated for an
if.comedy award, formerly known as the
Perrier award. Crosby performed stand-up as part of the
Leicester Comedy Festival in 2007 and 2008. He also performed during the
Melbourne International Comedy Festival in 2008. As part of Pappy's Fun Club, Crosby returned to the Edinburgh Fringe with
Funergy in 2008,
World Record Attempt: 200 Sketches in an Hour in 2009,
All Business in 2010, and
Last Show Ever in 2012. Each show was followed by a tour of the UK. Crosby was a regular contributor to comedy podcast
Answer Me This!, playing various characters in jingles and sketches. 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. Crosby is co-creator of the
BBC Three sitcom
Badults which ran for two series. In 2015 Crosby took another solo hour show to Edinburgh called
Smaller Than Life. The show notably included a semi-naked impression of Vladimir Putin. He co-devised and co-wrote the comedy panel show
Hypothetical for UK TV channel Dave. In June 2019, Crosby launched a new Sunday morning show on
Radio X with fellow comedian,
Ed Gamble. Crosby lives in Beckenham, which he asserts to be in Greater
London, with his wife and two children. == Television appearances ==