Waddington made his debut with the 1991 film
Edward II, where he portrayed title character
Edward II. He appeared in 1992's
Last of the Mohicans in a supporting role as Duncan Heyward. He also appeared in
Tim Burton's 1999 film version of
Sleepy Hollow as Mr Killian. He played a lead role as Jeff in
Steve Coogan's
The Parole Officer (2001). Waddington then starred as
Prasutagus in the 2003 film
Boudica. He also portrayed the
Duke of Buckingham (who, coincidentally, was related to Edward II) in the
Showtime series
The Tudors in 2007. He later appeared in the ITV drama
Vital Signs along with
Tamzin Outhwaite, and starred as
King Richard in the Series 2 finale of
Robin Hood. Waddington also starred as Wilfred of Ivanhoe in the 1997 BBC/A&E production of
Ivanhoe, based on the novel by Sir
Walter Scott. Waddington reprised his role as
Richard the Lionheart in the BBC/Discovery Channel drama documentary
Heroes and Villains: Richard the Lionheart (2007). From April to July 2010 he portrayed canteen head
Adam Fleet in
Waterloo Road. He featured in two Swedish films. In 2008 he played the role of
Arnold of Torroja in the film and mini-series
Arn - The Knight Templar and McCullen in
Agent Hamilton: But Not If It Concerns Your Daughter in 2012. In 2012 he appeared in the four-part ITV mini-series
Titanic. He is played the role of Marshall Redwick in the
Sky One series
Jamestown, which premiered in 2017. He also had a part in Thomas Vinterberg's 2018 political thriller
Kursk, based on the true story of a doomed Russian submarine. In 2022, he played The Scotsman in
Uncharted, opposite
Tom Holland and
Mark Wahlberg. In 2024, it was announced that Waddington was writing and directing a biographical film based on the life of snooker player
Jimmy White, with
Aneurin Barnard and
Ray Winstone signed on to star in the film. ==Personal life==