[1][2][3] Bailey first appeared to American television audiences in 2002 in the recurring role of Scott Wilson, assistant to Lea Thompson, in the Lifetime network drama, For The People.

[4] He later portrayed the comedic recurring role of Vincent, the flirtatious bartender from the 'Indigo Club' on the soap opera The Young and the Restless.

[5] Bailey starred in the feature film comedy, Meeting Spencer with Jeffrey Tambor and Jesse Plemons in 2011.

[10][11] In the early 1990s, Bailey originated the role of Pepito in the popular Madeline specials by Cinar Films for HBO, narrated by fellow Montreal native, Christopher Plummer.

[13] Finding notoriety in the worldwide video game market, the actor played the role of Deputy Staci Pratt in Ubisoft's 2018 commercial hit, Far Cry 5.