Taylor grew up on Sydney's Northern Beaches and North Shore and, (as with all The Chaser team except Craig Reucassel), attended a private school. Talking about his schooling at the Shore School in an interview once, he said that "It's not a school I have much respect for but in many ways it was the making of me" and that "there's nothing like a private school for breeding a good satirist". Taylor is also an atheist.

After completing secondary school, Taylor undertook an arts degree at the University of Sydney, and also studied playwrighting at NIDA. But at 21, he abandoned playwrighting and went to back to university to study journalism at University of Technology, Sydney. In 1997 he moved to Melbourne after the ABC offered him a journalism cadetship there.

For five years, Taylor worked as an ABC journalist, including two years as a court reporter. He covered cases including the murder of toddler Jaidyn Leskie, the fatal Longford gas explosion and the unsuccessful defamation action by the then Victoria premier Jeff Kennett against The Australian.Taylor then moved back to Sydney in 2001 to work full-time for The Chaser's newspaper, and ultimately became a Chaser member.

In 2001, Andrew Denton got hold of one of The Chaser's newspapers and gave them the opportunity to produce a television show, hence The Chaser team produced their first ABC Television program The Election Chaser, which covered the 2001 Australian Federal Election. 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. The program will also be available to download free of charge for a limited time.

Taylor also united with fellow Chaser Craig Reucassel to present the Triple J drive slot, Today Today in 2004—2005.

As part of his role on Today Today, Taylor wrote and voiced a weekly Coma FM sketch, satirising the formats and style of commercial radio. He also co-hosted the radio program Bloody Sunday with Reucassel in 2006 and 2007. During the shows Chris would regularly ask listeners to "go for broke" and vandalise Wikipedia pages. Tara Reid, Peter Overton and Wikipedia's own Wikipedia page were chosen targets. And in 2008 Taylor and Reucassel returned to present The Race Race, covering the US Presidential election. The show quickly became the number one podcast in the country.

Taylor also has the distinction of being Roy Slaven's official understudy at Triple J, broadcasting alongside HG Nelson on This Sporting Life and a Twenty20 cricket game on the couple of instances when Roy Slaven was absent.

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.

Taylor, who's often referred to as "Tayls" by his colleagues, is one of the main presenters on The Chaser's War on Everything. He is also the program's script editor and principal writer behind many of the show's segments, sketches and songs.

Appearance on Sunrise

In the The Chaser's War on Everything skit "Will You Divorce Me?", Taylor made a guest appearance on Sunrise, a live morning talk show on Channel 7. He said he had an announcement for his wife and ended up yelling "Get the fuck out of my life" at the camera. The appearance of authenticity of this clip made it appear as though the segment went live to air on Sunrise, but it only ever appeared on The Chaser's War on Everything. Taylor and the hosts admitted it was a staged event, filmed on the Sunrise set after one of their shows but the latter said the dialogue was improvised and were shocked by the profane punchline. A clip of this segment became an Internet phenomenon

The Tim Freedman Parody

Taylor sparked controversy with Tim Freedman, singer and songwriter of indie rock band The Whitlams. On 7 October 2007, Freedman posted a message on the band's official website, citing a parody of him which was written by Taylor, and had aired on 3 October 2007 episode of The War. The song was performed by fellow Chaser Andrew Hansen, and the lyrics implied that Freedman was obsessed with the Sydney suburb of Newtown, and that he continually referred to the area of Newtown in his own songs. In his message, Freedman alluded that the lyrics were indeed written by Taylor, and that the parody had been motivated by jealousy over a girl they had both dated Anna Skellern who was a non-contributing cast member in the first season of CNNNN. Taylor denied this, and said that the song had nothing to do with Skellern. Andrew Hansen in the commentary track for the season 2 DVD revealed that Taylor and Freedman had sorted the issue out and that everything between them was all good. 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.

The Eulogy Song

On 17 October 2007 episode of The War, Andrew Hansen performed The Eulogy Song, which was 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. The song became the target of significant media attention, with several radio and television personalities saying the song was in "bad taste", as well as then Prime Minister of Australia John Howard and then Opposition Leader Kevin Rudd expressing negative views.

In response to the attention, Taylor defended the song, stating that it was a legitimate skit about the way the media air-brushes celebrities in death. He also revealed it was a "watered down" version of the song which was previously performed on stage in the musical Dead Caesar. The original had a verse referencing Rene Rivkin, but it was replaced with a verse about Stan Zemanek.

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. The play was a musical comedy based on the life of Julius Caesar, featuring original music composed by Andrew Hansen, who also appeared in the play as Mark Antony and Lucius. The now infamous Eulogy Song was originally written for this production.