[1] In 2008, he played the role of Jacob in the Menier Chocolate Factory production La Cage aux Folles.
[2] 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.
[3] He joined the company of Guys and Dolls when the revival transferred to the Phoenix Theatre in March 2016, playing Benny.
[3][7] 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.
[8] In 2019, Pennycooke played Wilson in the musical drama Rocketman and in 2020, JJ in the BBC Comedy TV Pilot Bumps.