Sheldon was born into a family of carnival businesspeople, and he worked as a barker while receiving training in acting. After completing military service, he landed a role in the 1961 film The Guns of Navarone, and worked in small theatre productions. He shared a flat in London with three other unknown actors, who included Michael Caine and Sean Connery. Sheldon was discovered by Bunny Lewis while performing on-stage, and was quickly offered a recording contract with Decca Records, even though he had no previous experience performing as a singer.
Sheldon's first single was "Book of Love", which did not chart. The follow-up single was a cover of the tune "Runaround Sue", which became a hit record in the UK Singles Chart reaching No. 36, although Dion's version soon outstripped it in popularity both in the UK and the United States. His next single, "Your Ma Said You Cried in Your Sleep Last Night", became his highest charting hit in the UK at No. 29. Shel Talmy produced the next single, "Lollipops and Roses", which flopped, but with the tune "I Saw Linda Yesterday" he managed to crack the UK Singles Chart for the last time in 1963 at No. 36, thus emulating his first hit's position.
After the middle of the decade, Sheldon returned to a career in acting, where he appeared on TV in Doctor Who, The Avengers and Triangle, and in films such as The Yellow Teddy Bears (1963), Some Girls Do (1969), Ryan's Daughter (1970), Soft Beds, Hard Battles (1974), Appointment with Death (1988) and Iron Eagle II (1988). He also published novels using the slightly fuller name of Douglas Sheldon. In 2007, his entire Decca discography was released on CD by Vocalion Records.
- "Book of Love" (1961)
- "Runaround Sue" (1961) UK No. 36
- "Your Ma Said You Cried in Your Sleep Last Night" (1962) UK No. 29
- "Lollipops and Roses" (1963)
- "I Saw Linda Yesterday" (1963) UK No. 36
- "Mickey's Monkey" (1964)
- "Albums by Doug Sheldon: Discography, songs, biography, and listening guide". Rate Your Music. 1964-01-25. Retrieved 2014-08-27.
- "Who is Doug Sheldon?". Omnilexica.com. Retrieved 2014-08-27.
- Bruce Eder, Doug Sheldon at Allmusic
- "Rock and roll | Sue Records UK". Suerecordsuk.wordpress.com. Retrieved 2014-08-27.
- Roberts, David (2006). British Hit Singles & Albums (19th ed.). London: Guinness World Records Limited. p. 495. ISBN 1-904994-10-5.
- "Doug Sheldon". IMDb.com. Retrieved 2014-08-27.
- Bruce Eder (2007-10-15). "Craig and Doug at Decca: Singles Compilation 1957-1961 - Craig Douglas,Doug Sheldon | Songs, Reviews, Credits, Awards". AllMusic. Retrieved 2014-08-27.
- Search for "Doug Sheldon" performed at Everyhit.com database on September 29, 2008.