After decades of alcohol addiction and clinical depression he became destitute; he was assisted by music industry benevolent society, Support Act, from 2001.
In early 1974, Shakespeare was in Albert Studios where producers and songwriters, Vanda & Young (ex-The Easybeats), were trying to record "Can't Stop Myself from Loving You", however, the singer they were working with was unable to reach its high notes.
A number of guest hosts including Shirley Strachan, John Paul Young and Daryl Braithwaite compered the show in its early years on an ad hoc basis.
In November 1974, Shakespeare released his debut album, Can't Stop Myself from Loving You, produced by Vanda & Young for Albert Productions.
[4][7] In 1975 John Cave was convicted of statutory rape of a 15-year-old girl from his Melbourne fan club, and he received two years probation.
[4][12] A temporary revival of his singing career occurred in 1990 when listeners of Triple M Melbourne voted "My Little Angel" as the daggiest song of their generation and a cover version was provided by the Melody Lords.
For his day job, Shakespeare was a car detailer at a Holden dealership in Arncliffe, New South Wales for most of his working life.
Mental illness and alcoholism took its toll on his personal life and by 2001, Shakespeare was homeless and lived in a ticket booth at an oval next to St George's Leagues Club in Kogarah, where he was found and assisted by Lindy Morrison (ex-The Go-Betweens drummer) of Support Act Limited, a company concerned with assisting artists in hard times.