He is possibly best known for his starring role in the British TV drama The Roads to Freedom, as Daniel, alongside Michael Bryant.

He is also known for his role in the 1968 American film Star!, as Noël Coward (Massey's godfather), for which he won a Golden Globe Award and an Oscar nomination.

[3] He made a major impression as an adult as Laurence Olivier's son-in-law in the stage and screen versions of John Osborne's The Entertainer (film in 1960).

[5] Other highlights of his career were his stage roles, especially that of the German conductor Wilhelm Furtwängler in Ronald Harwood's Taking Sides; Massey was nominated for the 1996 Olivier Award as Best Actor.

In 1970 Massey played the role of the openly gay character Daniel, alongside a cast headed by Michael Bryant as Mathieu in the acclaimed multi-part BBC adaptation of Jean Paul Sartre's The Roads to Freedom.

[11] Other television highlights of Massey's career include The Crucible on the BBC (1981) as Reverend Hale,[12] The Golden Bowl (1972) as the Prince, in the Inspector Morse episode "Deceived by Flight" as Anthony Donn, again with John Thaw, the BBC adaptation of Molly Keane's novel Good Behaviour (1983) as the Major, and his performance as an AIDS patient in Intimate Contact (1987).