Simon was born on 13 October 1950 and brought up in north London. He is a founding member of Fairport Convention, joining the band at its inception in 1967. As a teenager, he met local musician Ashley Hutchings. They – with others – formed Fairport Convention, taking the name from Simon's house 'Fairport' where the band rehearsed. Fairport Convention became hugely successful after vocalist Sandy Denny joined the band. However, after Sandy left Simon found himself taking a more prominent role on stage. He also became more involved in studio work and production. During the 1970s, Simon took a four-year break from Fairport (supposedly he couldn't face playing "Sloth" anymore) working on various projects as both producer and musician, collaborating with Dave Swarbrick and The Albion Country Band among others. Simon rejoined Fairport in 1975 and has been the band's main guitarist and lead singer ever since. However, he has continued to work with other musicians including Dave Swarbrick, Ashley Hutchings, Richard Thompson etc and has toured with, among others, Beverley Craven and Art Garfunkel. Simon has also released two solo albums which were fairly recently reissued as a double set. Material from both of these albums has often been played live with Fairport Convention or Fairport Acoustic Convention with both "Rosemary's Sister" and especially "The Deserter" being strong favourites. Simon is still very active both in these bands and also tours with the Albion Christmas Band each year.