Solo Career
After The Sports had disbanded in late 1981, Cummings spent 1982 co-writing tracks with Ian Stephen (The Armchairs), and waiting out his contract. He released his debut solo single, "We all Make Mistakes" on Phantom Records, in January 1983 and followed with "Stuck on Love" in September. Cummings' debut album, Senso, released by Regular Records in August 1984, was produced by former bandmate Martin Armiger, and recorded with session musicians including, Armiger, Joe Camilleri and Pendlebury from his earlier bands. Senso spawned two dance pop singles, "Gymnasium" (July 1984) and "Another Kick in the Head" (October), with a non-album single "What am I Going to Do?" following in 1985.
His second album, This Wonderful Life released in September 1986, was a more personal and less busy recording, which was produced by Cummings and provided two singles, "Speak with Frankness" (July) and "Love is Crucial" (October). Cummings dueted with Pendlebury (by then ex-Slaughtermen alongside Ian Stephen) on "She Set Fire to the House" with John McAll on Piano released in September 1987. For his third album, Lovetown released in January 1988 on Rampant Releases, Cummings formed Stephen Cummings' Lovetown (aka Stephen Cummings and Lovetown) with Rebecca Barnard on backing vocals, Mick Girasole (also in The Black Sorrows alongside Camilleri) on bass guitar, Peter Luscombe (also The Black Sorrows) on drums, Shane O'Mara on guitar and Pendlebury on guitar. It "was a very subtle, alluring, personal and mostly acoustic album full of conversational, narrative vignettes". The album, produced by Mark Woods and Cummings, provided two singles, "Some Prayers Are Answered" in February and "My Willingness" in May.
Cummings changed labels to True Tone Records for his next album, A New Kind of Blue, which was released in March 1989 and produced by Cummings and O'Mara. It spawned three singles, "A Love is a Life" in October 1988, "Your House is Falling" in February 1989 and "When the Day is Done" in July. The album provided Cummings with his only Australian Recording Industry Association (ARIA) Award, winning "Best Adult Contemporary Album" in 1990.
For his fifth solo album, Good Humour, Cummings returned to his earlier dance and funk sound from his Senso album, using a backing band of Barnard, O'Mara and Nick Smith (ex-Kevins) on backing vocals, with additional session musicians from Sydney jazz outfit The Necks, and Robert Goodge (I'm Talking) on guitar, drum programming and co-production (for two tracks). The album, produced by Cummings and O'Mara, peaked at #40 on the ARIA Album Charts in March 1991. "Hell (You Put Me Through)", which peaked at #33 after its January release, was followed by a cover of Sly Stone's "Family Affair" and then "Stand Up (Love is the Greatest)". Cummings has supplemented his income by writing advertising jingles: he co-wrote Medibank Private's theme "I Feel Better Now", with Goodge.
Cummings' next album, Unguided Tour, produced by Cummings and O'Mara for Polygram Records, was issued in 1992 and provided three singles. Steve Kilbey of The Church produced Falling Swinger, Cummings' seventh solo album released in August 1994. The single, "September 13" appeared in July and is titled for Cummings' birthday, which he shares with Kilbey. Later in 1994, the Toni Childs and Cummings duet, "Fell from a Great Height", was released as a single, it later appeared on Childs' compilation album, Best of Toni Childs in 1995. Kilbey also produced Escapist in September 1996, which contained "countrified ballad `Everything Breaks Your Heart' to the psychedelic-tinged mantra `Sometimes'". Also in 1996, Cummings published his first novel, Wonderboy, which deals with relationships especially those between a father and son.
On 14 November 1998, Cummings and, a briefly reformed, The Sports performed at the Mushroom Records 25th anniversary concert. His next solo album, Spiritual Bum, had Cummings as record producer and was issued in June 1999. He returned to an acoustic, melancholic sound. Cummings also had his second novel, Stay Away from Lightning Girl, published in 1999, which described an aging musician and his band. In 2001, he released Skeleton Key followed by Firecracker in 2003, Close Ups in 2004, Love-O-Meter in 2005, Space Travel in 2007, and Happiest Man Alive in 2008. On 1 May 2009, his memoir, Will it Be Funny Tomorrow, Billy? : misadventures in music was printed, which his publishers described as a series of anecdotes from his childhood through thirty years of the music business and his family relationships. In October 2010, his 1988 album Lovetown was listed in the top 40 in the book, 100 Best Australian Albums.
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