[9] He then went to Richmond College and entered the National Youth Theatre's summer course.

[9] By 2015, he was an aspiring actor working at a coffee shop in Waterloo, London.

[10] Weeks after Whitehead finished with Dunkirk, he began work with Richard Eyre's film The Children Act, opposite Emma Thompson and Stanley Tucci, which premiered at the Toronto International Film Festival in September 2017.

[14] In 2018, Whitehead starred in the Black Mirror television series’ interactive stand-alone film Bandersnatch, as lead character Stefan Butler.

In 2019, Whitehead appeared in Sebastian Schipper's drama Roads, and the Martin Scorsese produced Port Authority.