[1] Before graduating from RADA, Pickup won a part in the BBC series No Bananas, playing the role of Kaye Bentley, her first professional engagement.
Other major theatre roles followed, including Irina in Mike Poulton's translation of Three Sisters for Bill Bryden, Olivia in Twelfth Night for Terry Hands, Helena in All's Well That Ends Well for Irina Brook,[3][4] Portia in Julius Caesar for David Farr at the RSC, Sylvia in The Two Gentlemen of Verona and Helena in A Midsummer Night's Dream also for the RSC.
[citation needed] Pickup appeared with her father for the first time in 2008 in an episode of Midsomer Murders:The Magician’s Nephew and played Molly, the central role in her mother's first screenplay "G - Litter" in 2015.
Pickup starred at the Criterion Theatre in The 39 Steps and has worked with Sir Peter Hall several times, including his 2009 revival of Bedroom Farce.
She was nominated for a Critics' Circle Best Actress Award for her performance in Miss Julie with Stephen Unwin at the Rose Theatre, Kingston.