Rupert grew up on Guernsey, where he was an Elizabeth College student, but he began his musical training at the age of nine as a chorister, and later head chorister, at Southwell Minster in Nottinghamshire.
He took up flute and was awarded a scholarship to study at Trinity College of Music with Michael Cox, gaining a BMus degree. He subsequently won a Daily Telegraph Young Jazz competition for instrumental solo, ensemble and composition. In 1993 Rupert became a member of the National Youth Wind Orchestra, performing concerts throughout the UK and Europe.
He also played flute with a number of other orchestras, including the Channel Islands Youth Orchestra and the Guernsey Symphony Orchestra – with the latter he toured most of Central Europe and Scandinavia.
Rupert joined NYJO on flute in 2000 and played with the band until 2009, featuring on the albums Jasmine and Jazz In Film. During this time he also formed and fronted his own Alpine Big Band, playing primarily alto saxophone and flute.
As one of the UK’s top jazz saxophonists and flautists he is regularly in demand for gigs and sessions. He is a member of Q The Music, a band dedicated to the music of the James Bond films, and in February 2015 he completed a stint in the pit band of City of Angels, at the Donmar Warehouse, alongside fellow NYJO alumni Laurence Ungless, Jon Stokes and Jay Craig.