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Bailey began his career as a child actor in Royal Shakespeare Company productions, and by eight, he was performing as Gavroche in a West End production of Les Misérables. He has since starred in contemporary plays such as South Downs in 2012, The York Realist in 2018, and Cock in 2022; in classical plays like the Royal National Theatre's Othello in 2013 and Chichester Festival Theatre's King Lear in 2017; as well as in musicals, namely the London revival of The Last Five Years in 2016 and the West End gender-swapped revival of Company, for which he won the Laurence Olivier Award for Best Actor in a Supporting Role in a Musical in 2019.

On screen, Bailey starred in the action-adventure series Leonardo (2011–2012) and the musical-comedy Groove High (2012–2013) before becoming known for his roles in the crime drama Broadchurch (2013–2015), the satire W1A (2014–2017), and the comedy Crashing (2016). He gained international recognition for his starring role in the Regency romance series Bridgerton (2020–present). Bailey's role in the romantic drama miniseries Fellow Travelers (2023) won him a Critics' Choice Television Award for Best Supporting Actor and a nomination for a Primetime Emmy Award for Outstanding Supporting Actor. He has since played Fiyero in the two-part musical fantasy film Wicked (2024–25).