Derek was a washboard player in a skiffle group in 1956 and later a drummer in a rock and roll band, after which he spent 10–18 years working in the accounts department of the confectionery firm J. S. Fry & Sons, later part of Cadbury.

[6] DJ Derek became a well known regular and respected feature in Bristol's music scene, referred to as a "legend" by many sources including the city's elected mayor George Ferguson.

[4][6] In June 2006 he released a compilation of his favourite tracks titled DJ Derek Presents Sweet Memory Sounds, through Trojan Records.

[21] In December 2015, Derek's family said that a man matching his description had been seen fleeing a pub in Thornbury following an altercation; Avon and Somerset Police said that their investigations into his disappearance were continuing.

While his family noted an "uncanny" resemblance,[23] Avon and Somerset Police later announced that they had located and spoken to the man photographed, and confirmed that he was not Derek.

[31] In March 2016, Bristol pub The Farm in St Werburghs, one of Derek's regular haunts, revealed they were hosting an auction to raise funds for a mural near his home.