[2] At 14 years old, he started playing guitar and his early influences were Pearl Jam, Alice in Chains, The Meanies and Cosmic Psychos.

[3] In August 1996 Lindsay McDougall joined Australian punk rock band Frenzal Rhomb after original guitarist Ben Costello left to attend university and become an animal rights activist.

[9][10] Also that year, McDougall and Whalley formed a side-project, Self Righteous Brothers, as an alternative rock group and issued the album, Love Songs for the Wrong at Heart on Shock Records.

[12] For the album, McDougall provided lead vocals, acoustic and electric guitars, banjo, piano, violin, viola, cello, pan flute, glockenspiel, zither, timbales, and cymbals.

In December 2010, they joined the No Sleep Til Festival Tour with punk and metal bands: Megadeth, Descendents, NOFX, Gwar and Dropkick Murphys.

[15] In January 2005 Lindsay McDougall and Whalley took over as hosts of national youth radio station, Triple J's Breakfast Show, under the name, Jay and the Doctor.

In January 2007, former Lunch presenter, Myf Warhurst, joined McDougall and Whalley as a permanent member of the Breakfast Show team.

[17] The show continued The Friday Fuck Wit segment and included the radio serial, Claytron, produced by Australian comedian Sam Simmons.

[23] At the start of 2010, McDougall asked listeners to take pictures of their "awesome stuff, precious things and treasured items"[24] to help decorate his new blog and Triple J website.

In July and August it was broadcast from Woodford, Queensland for Splendour in the Grass, the program included live sets and interviews with bands from the festival line up.

[25] Guests on the 2010 program included Jack White, Lou Reed, Bret Easton Ellis, Chuck Palahniuk, MUSE, Phoenix, Arcade Fire, Damon Albarn, Mumford & Sons and Dizzee Rascal.

In August, McDougall asked for donations to United Nations High Commissioner for Refugees – he staged a homage to Children Collide's music video for "Loveless" while he had his long hair cut off.