He has released several albums of musical comedy, toured Australia extensively, been nominated for an ARIA Award and published books about his experiences in the entertainment industry.

The Bedroom Philosopher began in 2002, Heazlewood submitted a three-minute radio piece for the ABC Heywire competition about his passion for folk music, which led to him becoming a regular guest on Triple J's The Morning Show.

[2][3] He also filmed two pilot episodes of The Bedroom Philosopher Show for ABC Fly TV, a now defunct digital youth television station.

[4] He also secured his first major musical gig, playing support for Bodyjar and The Bumblebeez at Triple J's Unearthed concert later that year.

[11] The Bedroom Philosopher's first album, Living on the Edge of My Bed featured tracks which had earlier been played on The Morning Show, and was released in 2003.

In 2005 the Bedroom Philosopher released his first retail and studio album, In Bed with My Doona,[12] produced by his uncle Ken Heazlewood.

After performing at Perth International Arts Festival The Bedroom Philosopher completed his second album Brown and Orange with producers Chris Scallan and Martin "Moose" Lubran, released in February 2009.

[23] The music video for song "Northcote (So Hungover)" was created by director Craig Melville and produced by David Curry.

The video satirises hipster culture which is currently popular in inner-city Melbourne, with humorous stereotypes and pretension thought to be present in neo-hipsterism.

The Bedroom Philosopher has since recorded a version of the song composed entirely of comments made on the film clip's YouTube page.

[29] 2011 saw the release of the songs "Leaving My Hairdresser" and "Tram Inspector", the film clip for the latter charting at 19 in Rage's Top 100 Filmclips of 2011.

[35] From 2005 to 2006, Heazlewood was a full-time writer for the Network Ten sketch comedy program The Ronnie Johns Half Hour.

The E-book was published by Affirm, earning praise from Tony Martin, Benjamin Law, Dave Graney and Neil Gaiman.

Heazlewood spent 2013 and much of 2014 working on his non-fiction book Funemployed, about the challenges faced by people in the Australian creative industries was published in May 2014.

The "Funemployed LP" album (later released as The Bedroom Philosopher) features spoken word pieces from interview subjects Brian Ritchie, Tim Rogers and Sam Simmons.