Raised in Wakefield, West Yorkshire in the United Kingdom, Bailey has a natural Yorkshire accent, and he also has an ear for other regional British dialects (Cockney, Scouse, Mancunian, Geordie and Scottish). Bailey starred in Nancy From Now On, which won the Audience Choice Award for Best Short at Toronto's imagineNATIVE Film Festival as well as the Creative New Zealand Emerging Talent Award. In the film, Bailey plays a young Māori takatāpui boy, with a desire to become a drag queen. Jane Campion said: "I liked this film for its light-handed yet authentic expression of alt-sexuality and the unforgettable charm of the lead, Bailey Poching." He is also a newly-minted pro stand up comedian, who recently reached the Grand Final of the prestigious RAW Comedy Quest. Bailey also trains in improvisation with Bull Rush Improv. Bailey has a strong commitment to and passion for telling diverse and interesting stories about Māori and Pasifika.