[2][3] The song "No Aphrodisiac", co-written by Freedman,[4] was their breakthrough hit in 1997;[5] their top four ARIA albums by sales are Love This City (1999), Torch the Moon (2002), Little Cloud (2006), and their compilation album Truth, Beauty and a Picture of You: Best of the Whitlams in 2008.

[5] A highlight of his career was receiving an ARIA Music Award for 'Song of the Year' in 1998 from the former Australian prime minister Gough Whitlam—after whom his band is named.

[9] In an interview, which aired on 612 ABC Brisbane on Friday 29 September 2006, Freedman said he became a pianist "by mistake" after quitting law school.

Since late 2006, Tim has been the host of the music chat show The Tim Freedman Sunday Session at 6pm, airing Sunday nights on the Sydney radio station Vega 95.3 (now known as Smooth FM).

[citation needed] In 2014, he started writing as a music critic for a newly founded print and digital newspaper, The Saturday Paper, to help support the paper's growth, which has since grown to a circulation of 900,000 as of 2021.