In 2004, O'Brien appeared in the controversial film 9 Songs. According to The Guardian, 9 Songs was the most sexually explicit mainstream film to date, largely because it includes several scenes of real sexual acts between the two lead actors. His role is highly unusual in that he had unsimulated and very graphic sex with his co-star Margo Stilley including genital fondling, female masturbation, with and without a vibrator, penetrative vaginal sex, cunnilingus and fellatio. During a scene in which Stilley stimulates his penis with her hand after performing fellatio on him, he became the only mainstream British actor who has been shown ejaculating in a mainstream UK-produced feature.