In 1990, he started in television as a reporter for Network Ten on Good Morning Australia with Kerri-Anne Kennerley and Mike Gibson.

He subsequently made a return to Network Ten, initially taking up a television role on Good Morning Australia (GMA), before becoming a host and presenter on many programs including Totally Wild, The Chilli Factor, The Big Breakfast, Airtime Basketball and the Vodafone Beach Volleyball tour.

His sports coverage has included the Commonwealth Games, Melbourne Cup, Bathurst 1000 and Indycar racing.

Bailey stated of his sacking:20 minutes after I was sacked from Channel 10, my phone rang, and before I had a chance to fall down, a bloke by the name of Benny Fordham picked me up.

'[8] On 21 September 2020, he commenced presenting the weather for morning and drive programs on Sydney radio station 2GB until July 2021, where he decided to move to the Gold Coast.