After leaving his job as a lawyer, Pickering appeared in the Melbourne International Comedy Festival (MICF) in 2002[2] with Michael Chamberlin in Boiling Point,[3] a show which earned them the Piece of Wood Award.[4] Prior to this, Pickering had appeared with the sketch comedy group Enter the Datsun in the MICF in 1998, 1999 and 2002.[5] In 2003, Pickering and Chamberlin teamed up again in Boiling Point 2,[6] the pair also appearing the same year with fellow comedian Terri Psiakis in Equal Third.[7] In 2004, he appeared in Revolver.[8] In 2005, Pickering launched Betterman at the MICF, a show he went on to tour in New Zealand[6] where he won the Best International Act in the New Zealand Comedy Guild Awards, and also at the Edinburgh Fringe Festival where he was nominated for the Perrier Award's Best Newcomer. In 2006 he presented his show Auto at the Melbourne International Comedy Festival, receiving a nomination for the Barry Award.
For the April 2013 Melbourne International Comedy festival, he co-hosted with Waleed Aly a series of shows titled The World's Problems Solved.[9]
Pickering has also worked in Australian radio, including youth radio station Triple J[7] from 2001 to 2003. He has been a pundit on Fighting Talk on BBC Radio 5 Live in 2006 and 2007.
In December 2022, ABC announced that Pickering will host Breakfast on ABC Radio Melbourne on Friday from January 2023.[17][18] He remained in the position until December 2023 as it was announced that Sammy J will return to hosting Breakfast five days a week.[19]
Literature
Pickering published his first book, Impractical Jokes, in 2010.[20]
As co-host of Channel Ten's The Project, Pickering claimed to have voted Liberal "once".[24] Pickering has hosted the ABC political and cultural commentary program The Weekly with Charlie Pickering since 2015. New Matilda describes the program as "a satirical news program with a progressive bent".[25] On the program, Pickering has used his editorials to support halal certification and gay marriage, and to speak out against the detention of asylum seekers.[26][27][25] He has been a strong critic of the Catholic Church. In June 2018 he angrily denounced the Catholic seal of the confessional.[28] In March 2019, he denounced and ridiculed people who questioned the guilt of Cardinal George Pell in a segment of his program he called "The Pedo Files".[29] Pell's conviction was overturned by the High Court in April 2020.[30]