The Early Years

Born on 15 October 1944 in Birmingham, John Thomas Woolley loved music from an early age, playing ukulele and singing, dancing, joking and dressing up at the Working Men’s club where his uncle was a steward. His father, Charlie, was a coal miner which gave John the chance to be a regular entertainer on the colliery seaside charabang where he sang until his throat was sore.

In 1958 his parents gave in to his demands and bought him a guitar and he joined a local skiffle group.  He was soon performing five nights a week and every weekend. Never content to be just the singer or the guitarist, John Woolley wanted to be out in front, and so whenever the chance arose he would be joking with the audience.

Life On The Ocean Wave

Now using his nickname Sheb Woolley,  after the US Purple People Eater comedy country singer, it came time to look for a job. When the only proper job offer he received came from the National Coal Board he decided to look elsewhere, and in January 1960 he joined the Royal Navy.

During his Navy years he had plenty of opportunity to entertain, and he did just that, appearing solo or with ships groups all around the world, often performing alongside international stars such as Liza Minnelli, The Dave Clark Five and Matt Monroe. More official entertainment jobs soon came his way, Ship’s Radio and Television production plus service club organisation.

Stand Up and Comedy Songs

His first venture into a folk club came in 1969, when he was inspired by Bob Dylan and the songs of the American Depression. He started writing his own songs and found he had a natural flair for humour and soon began to add jokes and monologues into his act. By 1973, he was still a naval gunnery instructor, but also performing as a folk comedian. His showbusiness success meant that by 1975 he decided to leave the forces to concentrate on his performing career.

By now he was known as Shep Woolley, a name change given to him by the Navy as his surname needed a name with a sheep connection, and he successfully applied for New Faces, an audition he decided to take as a bet.

After his appearance on New Faces on 10 May 1975, he used his experience on ship’s radio and television to secure a presenting job on a new local independent radio station, Radio Victory, which had opened in Portsmouth.  He presented the folk show for the next 10 years until Radio Victory lost it’s franchise.  His radio role did not however stop him from performing and he still appeared at festivals, clubs and theatres with both his one man show and in supporting concert roles for Alan Price, Joe Brown, Steeleye Span and Lindisfarne.

Back to the World

When his radio career came to a forced end he picked up on a request to perform standup in Hong Kong and following the success of his show he was soon offered ‘gigs’ in Singapore, Bermuda, Canada, Indonesia and the Arabian Gulf.

Shep’s next venture came to him by accident when in 1989 he made a comment to the organiser of an event in the south of England, that he thought musical events were not running very smoothly and did offer good value for money. The organiser challenged Shep to do it himself next year and he did just that.  

He has since been involved in supplying and arranging musical entertainment for the south of England leg of the Tour De France, P&O Cruises and the Bude Folk Festival. He has also kept his Navy links active by organising events aboard HMS Belfast, Portsmouth International Festival of the Sea, Maryport Sea Song Festival, Newlyn Deep Sea Fisherman’s Festival and Navy days events in Portsmouth and Devonport.

TV and Recording Work

As an actor he has appeared in numerous television plays and films, which included playing a sailor in the 1984 BBC drama Tenko. He has also been known to pull on a dress and pop on a wig to take on the role of dame in pantomime, a role that has been very popular with audiences, including his Widow Twanky alongside Alvin Stardust in Fareham in 2002.

He has a number of long-playing albums to his credit, a couple of minor hit singles, and released a new album in 2016, Sailors on a Train.

Shep was still actively performing as recently as December 2019 when he presented his evening of songs and stories with a festive touch at Gosport Discovery Centre, Hampshire.