Paul Dempsey and the Joy of Letting Songs Loose

What makes a great cover version? For Paul Dempsey, it is not fidelity. It is risk.

In Episode 42 of On The Record, Brian Wise and Michael Mackenzie welcome the Something for Kate frontman to discuss Shotgun Karaoke, his disarmingly loose—and increasingly popular—solo covers project.

Across two albums and a growing run of sold-out shows, Dempsey has turned the familiar songs of Cher, Bruce Springsteen, Phil Collins, R.E.M., Hüsker Dü, Tanita Tikaram and more into a rolling invitation for audiences to sing, shout and occasionally rescue him from a forgotten lyric.

The project began almost by accident.

During a lengthy Something for Kate tour in 2013, Dempsey’s bandmates challenged him to learn songs quickly backstage, then livestream the results. At the end of the run, he had amassed a clutch of spontaneous performances and took them into a studio, recording them live with little more than guitar and voice.

The first Shotgun Karaoke album followed; a second instalment arrived last year.

Dempsey calls the approach “brutalist covers”: stripped of the spectacle and the sonic furniture of the originals, with no attempt to replicate them.

That is precisely its appeal.

A song as oversized as Springsteen’s “Born to Run”, he says, becomes an exhilarating absurdity when one performer walks onstage with an acoustic guitar and attempts it alone.

The broader conversation becomes a timely examination of what audiences seek from live music.

Dempsey argues for unpredictability in an era of click tracks, backing tracks and perfectly calibrated performances. Wise finds common ground in Bob Dylan, whose restless reworkings can frustrate devotees of the original recordings but keep songs alive.

The alternative, as Dempsey sees it, is a live show that’s technically immaculate—and entirely without danger.

There are rules, however.

Dempsey chooses only songs he genuinely loves, and he performs them in their original keys. That means testing the outer edges of his range, from Leonard Cohen’s depths to Cher’s heights.

Lyrics matter just as much: a song must carry emotional truth, whether it is an enigmatic classic such as R.E.M.’s “Losing My Religion” or the sharply drawn narrative of Bright Eyes’ “Light Pollution”.

The conversation also returns to songwriting itself—an activity Dempsey describes as perpetually difficult.

Even after writing close to 200 songs, he says, the objective remains to surprise himself and evade familiar patterns.

His growing collection of synthesisers is part of that effort. Using them is a way of disrupting the muscle memory developed over four decades on guitar and finding new routes into the unknown.

There is lighter business at the top of the episode. Wise, fresh from the MCG, and Mackenzie, cinema-bound instead, consider Kylie Minogue’s grand final appearance and the place of polished spectacle in live entertainment.

They also welcome the return of Americana songwriter John Craigie, whose 2027 Australian dates follow the release of his new album I Swim Here.

Mackenzie is taken by Craigie’s intimate songs and his solo live readings of Beatles material—proof that an interpretation can honour a song without treating it as museum property.

On screen, Mackenzie recommends Tony, a dramatisation of Anthony Bourdain’s early life in a kitchen apprenticeship, whilst Wise is absorbed by an ABC documentary series on Tony Blair and the shadow cast by the Iraq War.

He also points viewers to The Dropout, the drama charting Theranos founder Elizabeth Holmes’ rise and collapse.

But Dempsey supplies Episode 42’s central refrain: that a great song can survive a minimalist approach.

It can be handed to an audience that knows the chorus better than the performer. Because If it still connects, it’s doing its job.