[citation needed] After leaving RADA, Macfadyen became known in British theatre primarily for his work with the stage company Cheek by Jowl, for which he played Antonio in The Duchess of Malfi, Charles Surface in The School for Scandal, and Benedick in Much Ado About Nothing.

In 2005, he played Prince Hal in Henry IV, Parts One and Two at the Royal National Theatre, with Michael Gambon in the role of Falstaff.

[citation needed] A TV breakthrough came when he appeared as Hareton Earnshaw in an adaptation of Wuthering Heights, screened on the ITV network in 1998.

Also in 2001, he earned acclaim for his starring role in the BBC Two drama serial Perfect Strangers, which was written and directed by Stephen Poliakoff.

He also appeared in a short sketch for Comic Relief as the bridegroom in Mr. Bean's Wedding, alongside Rowan Atkinson and Michelle Ryan.

[citation needed] Macfadyen appeared in films including Enigma (released in 2001), and In My Father's Den, for which he received the New Zealand Screen Award for Best Actor.

[11] Macfadyen starred in Frank Oz's Death at a Funeral and the film Incendiary, based on Chris Cleave's novel alongside Michelle Williams and Ewan McGregor.

In June 2010, Macfadyen won a British Academy Television Award for Best Supporting Actor for his work in Criminal Justice.

[citation needed] In 2011, Macfadyen made a final cameo in Spooks, and in 2012, he played Oblonsky in Joe Wright's film Anna Karenina.

Macfadyen said he was "delighted to be embarking on another dose of Ripper Street – blood and guts, pocket watches and Victorian headgear, wonderfully dark, moving and mysterious story lines from Mr Richard Wardlow".

[18] In 2020, he appeared in the role of Major Charles Ingram in a three-part ITV drama, Quiz, based on the controversial coughing cheat scandal on Who Wants to Be a Millionaire?