Australian musicologist Ian McFarlane noted that he "has the capacity to lay his soul bare through his music, there is little pretence or adherence to fashionable measures in the band's delivery".

[5] For his final years of secondary schooling he attended Padua College on the Mornington Peninsula, where he was interested in playing basketball.

[3] Initially named Fish of the Day, the group were renamed after a gig at the Punter's Club, with Dempsey's Jack Russell dog, Kate, serving as the key inspiration.

[citation needed] By 2009, he had commenced recording an album titled Everything Is True in Los Angeles with mix engineer-producer Doug Boehm—in April 2009, the process was complete.

I think the only brand new hurdle is that most music is now simply there for the taking and a large proportion of the population seem disinclined to assign any value at all to the hard work and resources that went into creating it.

In 1998, he recorded an album of songs that he had written for a side project with other musicians (including Glenn Richards of Augie March) called Scared of Horses.

The Givegoods was the project of Tom Morgan (Smudge) and Andy Calvert, with assistance from Evan Dando (The Lemonheads) and Juanita Stein (Waikiki and Howling Bells).

[17] In October 2009 at the Melbourne International Arts Festival, Dempsey performed in the world premiere of the musical theatre production of Dirtsong, created by Black Arm Band.

Other performers included Trevor Jamieson (2014 only), Archie Roach, Lou Bennett, Jimmy Barnes, and Emma Donovan.

[22] In April 2010, Dempsey produced and mixed the third studio EP, Heavy Harm, by Sydney rock band, Papa VS Pretty.

[23] In October 2011, Dempsey performed with the Black Arm Band, Archie Roach, Mavis Staples, Ricki Lee Jones, and Joss Stone in "Notes From the Hard Road and Beyond", which was part of the Melbourne Festival and was held at The Sidney Myer Music Bowl.

[24] In January 2014, Dempsey produced the debut album, Humdrum Star, for six-piece Brisbane band Mosman Alder.

Based on the experiences of fellow musicians like Davey Lane (You Am I), Noga launched a Pozible campaign to pay for the anticipated recording costs of A$16,000.

Noga explained seven days prior to the close of the campaign in late November 2014 that he asked Dempsey to produce the album:"Paul and I have been friends for many years now and we've discovered that we work pretty damn well together.

[26] Dempsey appeared as a panellist on RocKwiz on 24 February 2007, performing a solo version of "Monsters" and George Michael's "Careless Whisper" with Kate Miller-Heidke.

He also appeared on Good News Week on 26 October 2009, performing the song "Fire" by Bruce Springsteen as part of the "Strange But True" segment.

He performed a solo version of "Survival Expert" from Something for Kate's album Leave Your Soul to Science as well as Hall & Oates "Out of Touch" with Emily Lubitz.

Later in the interview, Dempsey said that he is a fan of the astrophysicist Neil deGrasse Tyson, whose writings he has read, and whom he has seen in a live discussion with Brian Greene that was held in New York City.