His television work began with an episode during the second season of Doctor Who in 1964, for which he was paid £30. Pickup worked with Sir Laurence Olivier at the Royal National Theatre, most notably in Three Sisters and Long Day's Journey Into Night. In 1973, he starred in the BBC drama series The Dragon's Opponent, playing a World War II bomb disposal expert and also appeared in The Day of the Jackal. He played Lt. Harford in Zulu Dawn in 1979, portrayed Igor Stravinsky in Nijinsky in 1980, Prince John in Ivanhoe in 1982, and in 1983 he appeared opposite Penelope Keith in Moving. More modern roles have included parts in Hornblower, Hustle, Foyle's War, Midsomer Murders, Waking the Dead, The Bill, Silent Witness, and Inspector Morse. He is also a regular character in the BBC sitcom The Worst Week of My Life. His most recent appearance was in Holby City as Lord Charles Byrne.
Pickup gave a highly acclaimed performance as a decayed Russian aristocrat in the BBC series Fortunes of War, based on a work by Olivia Manning. He also provided the voice for Aslan in the BBC's adaptation of the Chronicles of Narnia and starred opposite Judi Dench in the 1989 Channel 4 serial Behaving Badly.
Pickup had the starring role as composer Giuseppe Verdi in the acclaimed The Life of Verdi, written and directed by Renato Castellani. In 2005, he had a supporting role in the family-based film, The Adventures of Greyfriars Bobby.
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