Faine began his professional career practising as a solicitor in various Melbourne law firms, and combined work with his love for cars by serving as a motoring reporter for a lawyers' magazine. He acted pro-bono for the Australian Democrats in a number of Court of Disputed Returns matters in the late 1980s with success. In 1989 he began working in radio, producing and hosting "The Law Report" on the Radio National channel of the ABC and, since that time, he has worked on various ABC radio and television programmes.
Since 1996, he has hosted ABC's local radio morning programme, from 8.30 am to 12.00 pm in Melbourne, including the "Conversation Hour", which is heard across Victoria from 11.00 am. Faine is known for vigorous debate, and for fostering conversation on politics, law, arts and sport. With high ratings that peaked in September 2002, he was found to be Victoria's top talk-show host (AC Nielsen survey), and in 2003 he received the ABC Local Radio 'Broadcaster of the Year' award. He has also worked on scripts for a number of television and feature films.
Together with his son Jack, who was aged 19 at the time, Faine used his long service leave in 2008 to drive overland from Melbourne to London, United Kingdom (UK).Ali Moore filled in for Faine on 774 ABC Melbourne for most of the last six months of 2008.