During the 1980s he starred in several successful television series, including Woodentop, Grange Hill and the BBC soap opera EastEnders, where he played Barry Clark from 1986 - 1989. Hailes' character was notable for being one half of the soap's first gay couple, introduced as the partner of the yuppie graphic designer, Colin Russell (played by Michael Cashman). In 1987 Hailes' character caused a great deal of controversy after EastEnders screened the first male-to-male kiss on a UK, prime time soap. The kiss prompted a multitude of complaints from angry viewers and a hostile backlash from the right wing press. Despite the fact that Hailes is heterosexual, he suffered from severe homophobia because of the homosexual role he played in EastEnders. He was attacked several times by members of the public who couldn't separate fact from fiction, which included being assaulted in a supermarket by a disapproving woman and strangled by a man at a petrol station. Even after he left the show he lost a job as a children's television presenter because of the so called "gay tag".
Since leaving EastEnders in 1989, he has gone on to appear in films such as The Killing Zone (1999); Murder with Mirrors and Waiting For A Killer. On television he has appeared in ITV police drama The Bill (2001;2002); Horizon; Nobody’s Hero; Sorry and the BBC’s production of Pinocchio.
Theatre appearances include Strip Poker; Doctor on the Boil; Gollocks and numerous pantomimes. He has also performed several plays for BBC radio and voice-overs and had a regular slot "Hailes Horrors" on the Steve Allen show on LBC radio.
As well as acting, Hailes also drives a London taxi.