Brother of the artist Harold Hailstone. After education at the Judd School, Tonbridge, Hailstone attended Goldsmith's college School of Art, under Clive Gardiner, then the Royal Academy Schools, with James Bateman and Walter Westley Russell. At the outbreak of World War II Hailstone joined the Auxillary Fire Service, drew his comrades and Blitz scenes and held an exhibition at the RA. In 1941 ha was asked to become an official war artist, initially attached to the Ministry of Transport.Later he painted convoys in the atlantic and Mediterranean, then in 1944 joined South-East Asia Command, painting Lord Louis Mountbatten and key members of his staff, pictures now in the imperial war museum. A gregarious, outgoing man, Hailstone went on to paint Sir Winston Churchill, Lord Olivier, Paul Mellon- he worked a lot in America-and members of the Royal family, but he as happily painted ordinary members of the public.