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Beginning his career in the 2000s, he played the title role in a 2004 production of the play Hamlet. Television roles followed this in Nathan Barley (2005), Criminal Justice (2008) and The Hour (2011–12); and film roles in Perfume: The Story of a Murderer (2006), I'm Not There (2007), Brideshead Revisited (2008), and Bright Star (2009).

In 2012, Whishaw played the title role in a BBC Two adaptation of Richard II, for which he won the British Academy Television Award for Best Actor. The same year, he appeared as Q in the James Bond film Skyfall (2012), going on to reprise the role in Spectre (2015) and No Time to Die (2021). He has voiced Paddington Bear in several projects since Paddington (2014). His other film roles in the 2010s include Cloud Atlas (2012), The Lobster (2015), Suffragette (2015), The Danish Girl (2015), and Mary Poppins Returns (2018).

Whishaw had a leading role in London Spy (2015). For his portrayal of Norman Scott in the miniseries A Very English Scandal (2018), he won a BAFTA, a Golden Globe Award and a Primetime Emmy Award for Outstanding Supporting Actor. In 2020, he had a leading role in the fourth season of the black comedy drama Fargo. He has since starred in the BBC medical drama series This Is Going to Hurt (2022), the short film Good Boy (2023), and the Netflix spy thriller series Black Doves (2024).