[5][6] Bailie portrayed "Skewer" in Cutthroat Island (1995), an English Judge in The Messenger: The Story of Joan of Arc (1999), and also "The Engineer" in Gladiator (2000).
[8] Bailie was born in Springs, South Africa on 4 December 1937, and went to boarding school in Swaziland (now Eswatini) before emigrating to Rhodesia (now Zimbabwe) with his family in 1952.
[12] Terry Hands was also a student at the same time, but had left earlier than Bailie and formed the Everyman Theatre with Peter James in Liverpool.
Amongst other roles, he played Tolen in The Knack..., Becket in Murder in the Cathedral, Dion in The Great God Brown, MacDuff in Macbeth and Lucky in Waiting for Godot.
[11] After a year there, Bailie returned to London and auditioned for and was accepted by Sir Laurence Olivier, joining the National Theatre.
There he portrayed "Florizel" opposite Judi Dench's "Perdita" in The Winter's Tale along with "Valentine" in The Two Gentlemen of Verona, "The Bastard" in King John, "Kozanka" in The Plebeians Rehearse the Uprising and "Leslie" in The Madness of Lady Bright.
He was cast as the lead in a show called Raindog, which required him to sing, dance, perform martial arts and gymnastics.
He is one of the Black Pearl crewmembers to survive the Kraken attack in the sequel Dead Man's Chest (2006) and also played Cotton in the third instalment: At World's End (2007).
Bailie found this to be a problem and proposed to director Gore Verbinski and writer Terry Rossio a storyline that Cotton was able to speak, but it was not included in the films.