Brought up in Leeds, Pennycooke trained for a dance career at the Northern School of Contemporary Dance in Leeds and at the
London Studio Centre. In 2008, he played the role of Jacob in the
Menier Chocolate Factory production
La Cage aux Folles. The production subsequently transferred to the
West End at the
Playhouse Theatre, and he was nominated for the
Laurence Olivier Award for Best Performance in a Supporting Role in a Musical. He provided choreography and musical staging for the musical
Soul Sister, which opened at the
Hackney Empire in 2012, before playing in the West End at the
Savoy Theatre and touring the UK. He choreographed and starred in
The Big Life which played at the
Apollo Theatre in the West End in 2005. He was nominated for Best Choreographer in a Musical at the 2006
WhatsOnStage Awards and was also nominated for Best New Musical at the
2006 Laurence Olivier Awards. He also choreographed
Porgy and Bess which played at
Savoy Theatre 2006 and was nominated for Best New Musical at the
2007 Laurence Olivier Awards. In 2014 he played Bobby in the West End production of
Memphis. He was nominated for the
Laurence Olivier Award for Best Actor in a Supporting Role in a Musical for his performance. He was cast in the dual roles of
Marquis de Lafayette and
Thomas Jefferson in the
West End production of
Hamilton, in the original West End Cast, which began previews in December 2017. He was nominated for the
Laurence Olivier Award for Best Actor in a Supporting Role in a Musical for his performance, along with fellow Hamilton cast members, Cleve September and
Michael Jibson. In 2019, Pennycooke played Wilson in the musical drama
Rocketman and in 2020, JJ in the BBC Comedy TV Pilot
Bumps. In 2022, Pennycooke performed as
Henri de Toulouse-Lautrec in
Moulin Rouge! at the
Piccadilly Theatre in the West End. He was a part of the show’s original West End Cast. The show was extended until July 2022. In 2023, he appeared as 'Other Samuel' in
BBC One miniseries
Boat Story. == References ==