Stephen wasn’t built for stardom, but around the time of Lovetown he was dubbed ‘The St Kilda Sinatra’. It was a fair description, though Stephen is undeniably a better songwriter. Stephen’s songs have been covered by artists far and wide including Jimmy Little, The Whitlams, Vika & Linda Bull and Weddings Parties Anything, and he has even collaborated with the Australian Dance Theatre.

After Stephen’s band The Sports disbanded in late 1981, Stephen embarked on a solo career, and released his debut solo album, Senso, in August 1984, produced by his former The Sports bandmate Martin Armiger.

In September 1986 he went on to release his second album, This Wonderful Life. This Wonderful Life was more personal and less busy than Senso, and was self-produced by Stephen himself. This Wonderful Life produced the singles, ‘Speak with Frankness’ and ‘Love is Crucial’.

Lovetown, Stephen’s third solo album, was released in January 1988, and was a very subtle, alluring, personal and mostly acoustic album full of conversational, narrative vignettes. Following Lovetown, Stephen changed labels and released A New Kind of Blue, which earnt Stephen an ARIA Award for Best Contemporary Album in 1990. Lovetown and A New Kind Of Blue provided the soundtrack to many music loving Australians in their early 20s.

For his fifth solo album Good Humour, Cummings returned to the dance and funk sound that was heard on Senso. Unguided Tour came along in 1992, produced by Cummings and Shane O’Mara, and was followed by Swinger in 1994, produced by Steve Kilbey of The Church, who also produced Swinger’s follow up Escapist in 1996.

In 1996, prior to releasing Swinger, Stephen published his first novel, Wonderboy. Wonderboy dealt with human relationships, especially those between a father and son.

In 1999 Stephen produced and released yet another album – Spiritual Bum. The album returned him to a more acoustic and melancholic sound. He also released his critically acclaimed second novel, Stay Away From Lightning Girl.

Spiritual Bum was followed by a slew of albums: Skeleton Key in 2001, Firecracker in 2003, Close Ups in 2004, Love-O-Meter in 2005, Space Travel in 2007, and Happiest Man Alive in 2008.

Cummings published his memoir, Will It Be Funny Tomorrow, Billy? in 2009, which was met with critical acclaim and described as “often hilarious if occasionally uncomfortable” by the Sydney Morning Herald. Will It Be Funny Tomorrow, Billy? led to the film documentary Don’t Throw Stones, which went on to premiere at the Melbourne International Film Festival.

Following the release of his memoir, Stephen continued to consistently release new music; Tickety Boo (a pop album produced by Billy Miller) came in 2009, Good Bones (a companion album to Close Ups) in 2010, an album of acoustic re-workings of songs from across his career, Reverse Psychology in 2012, and Nothing To Be Frightened Of in 2014.

Now, Cummings is gearing up for the release of his 20th solo album – Prisoner Of Love. Prisoner Of Love will be released in February on Stephen’s new label home, Bloodlines (Mushroom Group). For Prisoner Of Love, Stephen has reunited with Billy Miller, who produced Tickety Boo and Reverse Psychology, to produce the new album.

Prisoner Of Love is a dynamic-sounding album, though Billy says they let Stephen’s voice do the work: “The sound we were after? When you’ve got a great singer like Stephen, it’s pretty simple: everything we add is merely a support for that voice.”