[1] She became drawn to comedy in Year 5 when she appeared in a school musical production of Alice in Wonderland, in which she dressed as a bunny and pretended to fall asleep during the performance.

[4] In Australia, Flanagan has appeared on various television series including Full Frontal, The Project, Rove Live, The Weekly with Charlie Pickering, Have You Been Paying Attention?

[5][7] In 1989, Flanagan began her five-year stint as an advertising agency copywriter, creating campaigns for products such as Quik chocolate drinking powder.

[11] Her first attempt was a success and she then started her comedy career in 1994 doing stand-up at an open mic night at the Harold Park Hotel in Sydney.

[12] She also worked with author and screenwriter Sean Condon to develop his screwball comedy script Splitsville as a hook for a television series, which later evolved into an e-book.

[15][16] During her time in the UK, she regularly returned to Australia for short visits and appearances on television shows including Rove, Good News Week, Spicks and Specks and The Sideshow.

Flanagan took her stand-up internationally and performed at many major comedy festivals, including Edinburgh, Melbourne, Montreal, Kilkenny, Cape Town and Johannesburg.

[10] She starred in the Comedy Channel's 2009 TV special I Can't Believe It's Not Better[17] before joining The Project for segments on trending news topics.

[29] In March 2018, Flanagan released a book of personal and professional autobiographical stories called Bridge Burning and Other Hobbies.

[41] An accomplished master of ceremonies, Flanagan hosted many awards nights and provided after-dinner comedy for companies as diverse as Australia Post and the Australian Pharmaceutical Association.

Funds raised go to a Victorian not-for-profit charity animal rescue centre called Edgar's Mission Farm Sanctuary.

Flanagan hosted Yarn Spinning,[45] the opening event of Word Adelaide that celebrates two long-established Australian traditions: telling tall stories and going to the pub.

[46] She also featured in the event In Their Own Words, sharing the stage with Matt Lucas of Little Britain fame, Roly Sussex and musician Guy Pratt who performed in the bands Pink Floyd and Icehouse, to explore how the language of comedy has changed our lives and culture.

[53] Flanagan appeared alongside Ross Noble, Johnny Vegas, Simon Pegg, Tim Vine, Lee Mack, Matt Lucas, Rob Brydon, and Mark Williams in Coogan's Drugathon 2 to raise funds for the Chemical Dependency Centre (now named Action on Addiction) and RAPt (The Rehabilitation of Prisoners Trust).

[53] In 2009, Flanagan performed in Sydney at the Jerry Lewis Laugh For Life charity concert to support Muscular Dystrophy Foundation Australia (MDFA) in their fund raising and awareness efforts to fight the muscle wasting disease.

[54] Flanagan appeared alongside Australian comedians Julia Morris, Paul McDermott, Mikey Robins, Peter Berner, Fiona O'Loughlin and Tom Gleeson in the fundraising gig at Sydney's Enmore Theatre.