[citation needed] After completing secondary school, Taylor undertook an arts degree at the University of Sydney, and also studied play-writing at NIDA.

He covered cases including the murder of toddler Jaidyn Leskie, the fatal Longford gas fire and the defamation action by the then Victorian premier Jeff Kennett against The Australian.

They then went on to create other television shows for ABC TV, including two series of the Logie Award-winning CNNNN in 2002–03 (in which Taylor portrayed a chief commentator), and The Chaser Decides in 2004, which covered the 2004 Australian federal election.

In addition to his roles on television, Taylor has teamed up with Chaser colleague Andrew Hansen to write and star in a musical comedy series, The Blow Parade, on Australian radio station Triple J from 14 April 2010 until 26 May 2010.

In a notable instance while working at Triple J, Taylor agreed to streak across the grounds of the Sydney Big Day Out if the theme song from Media Watch polled in the 'Triple J Hottest 100' Countdown.

It was announced that in terms of votes counted, the Media Watch theme had in fact come in at number 7, and Taylor proceeded to do his nude run in front of a large group of spectators.

When the segment became a viral video, Taylor and the hosts admitted it was staged on the Sunrise set after one of their shows though the latter said the dialogue was improvised and unaware of the profane punchline.

In his message, Freedman said that the lyrics were indeed written by Taylor and that the parody had been motivated by jealousy over a woman they had both dated, Anna Skellern, who was a non-contributing cast member in the first season of CNNNN.

In the final episode of Season 3, Freedman even made a friendly cameo appearance on the show in a mock oral sex scene with Taylor.

On 17 October 2007 episode of The War, Andrew Hansen performed The Eulogy Song,[11] a song written by Taylor which satirised the lives of several deceased celebrities, including Peter Brock, Princess Diana, Donald Bradman, Steve Irwin, Stan Zemanek, John Lennon, Jeff Buckley, and Kerry Packer, expressing the view that people with flaws during life are often disproportionately hailed as "top blokes" after death.

As well as writing for The Chaser's War on Everything, Taylor wrote the play called Dead Caesar which premiered at the Sydney Theatre Company on 1 February 2007, and then had a one-month run in July 2007.