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In 1956 he hosted his own television series, For Members Only (broadcast on Associated Television), on which he interspersed interviews with newsworthy people with singing and playing the guitar.and also starred in the World War II film Sea Wife (1957), with Richard Burton and Joan Collins.Aside from earning a living, he saw acting as a way to improve his diction in preparation for when he finally entered Chambers.Grant's first acting role was for a Moss Empires tour in which he starred in a play titled 13 Death St., Harlem.in which he was the first to perform the song "Feeling Good", later covered by many others.He included a version of the song on his 1965 album, Cy & I.He joined 103 Squadron, based at RAF Elsham Wolds in Lincolnshire, becoming one of a seven-man crew of an Avro Lancaster.

Following service in the Royal Air Force during the Second World War, Grant worked as an actor and singer, before establishing the Drum Arts Centre in London in the 1970s.

Aware of the short supply of roles for black actors, Grant decided to increase his earning potential by becoming a singer, having learnt to sing and play the guitar during his childhood in Guiana.

This proved to be a successful undertaking and Grant soon appeared in revues and cabaret venues such as Esmeralda's Barn, singing Caribbean and other folk songs, as well as on BBC radio (The Third Programme and the Overseas Service).

He parachuted to safety into a field (south of Nieuw-Vennep, as he later found out) and was helped by a Dutch family, although a policeman subsequently handed him over to the German forces, and for the next two years Grant was imprisoned in Stalag Luft III camp, 160 kilometres (99 mi) east of Berlin.

(The camp is best known for two famous prisoner escapes that took place there by tunnelling, which were depicted in the films The Great Escape (1963) and The Wooden Horse (1950), and the books by former prisoners Paul Brickhill and Eric Williams from which these films were adapted.) Grant was eventually liberated by the Allied Forces in 1945.

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