[3] He then trained at the Royal Academy of Dramatic Art (RADA) in London, receiving the annual Bancroft Medal (silver) on graduation in 1964.

[8][9] He went on to star in the BBC drama series The Dragon's Opponent in 1973, playing Charles Howard, 20th Earl of Suffolk, a World War II bomb disposal expert.

[8][9] For this role and a 1983 BBC One adaptation of the play Waters of the Moon, Pickup was nominated for the British Academy Television Award for Best Actor in 1984.

[12] He went on to play Prince Yakimov,[13] a hapless, down-at-heel Russo-British aristocrat, opposite Emma Thompson and Kenneth Branagh in the BBC serial Fortunes of War (1987), based on a novel cycle by Olivia Manning.

Pickup starred in the short lived sit-com Not with a Bang, broadcast in 1990, and appeared opposite Michael Caine in Jekyll & Hyde the same year.

[3][14] Pickup's other roles included parts in Hornblower,[11] The Riff Raff Element,[15] Hustle,[16] Foyle's War,[7] Midsomer Murders, Lovejoy,[11] Waking the Dead,[17] The Bill, Silent Witness,[7] Sherlock Holmes,[16][failed verification] Doc Martin,[7] Inspector Morse,[11] The Rector's Wife,[15] the 1991 television adaptation of John le Carré's A Murder of Quality, and the BBC's 2004 drama for children, Feather Boy.

[20] He worked with Laurence Olivier at the Royal National Theatre, most notably as Baron Tusenbach in Three Sisters (1967) and Long Day's Journey into Night.

[4][24] Between March and August 2009, Pickup starred as Lucky in Sean Mathias's production of Waiting for Godot by Samuel Beckett opposite Sir Ian McKellen (Estragon), Patrick Stewart (Vladimir), and Simon Callow (Pozzo).

The tour opened in Malvern, Worcestershire, before travelling to Milton Keynes, Brighton, Bath, Norwich, Edinburgh, and Newcastle; its run at the Theatre Royal, Haymarket, was extended due to popular demand.

[15] He played Lt. Harford in Zulu Dawn (1979),[15] Igor Stravinsky in Nijinsky (1980),[26] Prince John in Ivanhoe (1982), and a government official in the James Bond film Never Say Never Again (1983) opposite Sean Connery.

In the 2017 film Darkest Hour, Pickup portrayed Prime Minister Neville Chamberlain as he cedes power to Winston Churchill in the early months of World War II.