His folk noir duo Jep and Dep were formed in 2012 with his domestic partner, Jessica Cassar on co-lead vocals, which have issued two albums.

[3] Gerling's early music was influenced by Pavement, Sonic Youth, Boredoms, Beck and Mercury Rev; writing with two guitars and drums.

The group provided experimental guitar pop, on their debut single, "Sedatives for Dead Radars" (1995) via Steve Pavlovic's Fellaheen Records label.

Gerling released four studio albums, Children of Telepathic Experiences (February 1998), When Young Terrorists Chase the Sun (September 2001), Bad Blood!!!

[16] He released a second EP, Sunray in the Rave Cave (2008) and an album Plankton Icke and Tina Turner David City Limits (late 2010).

"[23] Drew Larringfort of Rave Review caught their performance at Adelaide's Ed Castle, "[their] chemistry was incredible, feeding off each other with comical stage banter, joking with the 'hipsters' in the crowd and having a good old fashioned fun time.

"[28] In late 2014 the duo independently released their debut album, Word Got Out, which received 4 out-of 5 stars in reviews at Rolling Stone Australia,[29] and The Sydney Morning Herald.

[28] The duo adopt a film noir-aesthetic for their music videos, photographs and artwork and perform live with Cross on acoustic guitar and both on vocals.

[30] They supported Johnny Marr (the Smiths),[31] Jessica Pratt, Mirel Wagner,[32] Courtney Barnett,[33] Kristin Hersh from Throwing Muses, Gruff Rhys from Super Furry Animals[34] and Blackeyed Susans.

"[48] Rhythmns magazine's Chris Familton said "melancholy, plaintiff and downbeat in the vein of Nick Drake, Beck, Neil Young and Bill Callahan – yet he has found clever and unobtrusive ways to incorporate samples, synths, drum machines and effects that add a dystopian, sci-fi quality to the music".

[50] Rolling Stone Australia's Jonny Nail reviewed its track, "Highway Lights in the Night" and felt it is a "nostalgic synth-folk tilt, with his lonesome vocals, unmistakably his own.

Tyler Jenke from Rolling Stone Australia gave the album 4.5 stars out of 5 and explained, "blissful ocean of nostalgia, with hazy instrumentation, vocoded vocals, and echoed drumbeats and electronic blips immersing the listener in a devastatingly unique, yet warmly familiar world of musical euphoria.

Jenke stated "[it's] one which feels like a true breath of fresh air – an escapist's paradise made, fittingly, within Cross’ own studio utopia.

Cross puts on display his musicianship and creativity, creating something dark and elusive yet touched with a certain element of wry amusement.

[59] His influences include British folk revivalists Bert Jansch, John Fahey, Leo Kottke as well as newer artists, Ryley Walker and Steve Gunn.

It's a special thing to be able to create these wordless stories with such lyrical qualities, and in the context of contemporary Australian music this stands as a rare and quite unique album".

[66] On writing the album, Cross stated "Hearing Sonic Youth open tunings (Daydream Nation, Goo, Dirty) when I was a kid also was a gateway to John Fahey and Nick Drake solo guitar... it all made sense'.

Studying the acoustic guitar as a solo instrument even further, Cross this time brought in influences as far reaching as Doc Watson, Enya, Chuck Wild, Mississippi John Hurt and the Tacoma catalog to make something uniquely Australian.

[71] Jim Marks of the United States based Dusted Magazine said "At less than 40 minutes, Wizrad zips by, likely leaving listeners wishing for a longer record and digging into Cross's back catalog, which is well worth the effort.

He's no pale imitator either - he knows how to make his guitar sing and thrum, and his D.C Cross albums do also wander off into ambient interludes and field recordings, in fine American Primitive form".

[73] Cross released a music video for the album's track "A Harebrained Adventure of an Amateur Shaman" (February 2024), which was directed and created by Steve Hanft (the Cure, Elliott Smith, Beck).

Fans of Bachman, Isasa, Jones, Rolin, et al., take note"[76] and KLOF magazine said "Glookies is a more serious and no-frills record in the structure of the guitar playing, with Cross happy to allow the beauty of the tunes to shine.

[78] 24 October 2024, Cross released his debut album under the guise DREN CRSS, which is his strictly ambient, experimental and ecstatic instrumental music.