[citation needed] Day made his breakthrough as an actor in London's West End theatre, starring in Joseph and the Amazing Technicolor Dreamcoat when he replaced the departing Phillip Schofield.
[2] Day has appeared in many touring stage musicals, including Summer Holiday, Grease, The Rocky Horror Show, Hello Dolly and Great Expectations.
In Autumn 2012, he played HIV-positive gospel singer Gideon in the European premiere of the award-winning USA musical The Last Session, for which he was nominated for Best Actor in the Off West End Awards ("The Offies").
[citation needed] In 2014, he revisited his cabaret roots when he stepped in for his old friend, Joe Longthorne, who was ill.[9] He then guested on the Holby City Christmas Special, playing panto dame Michael Evans.
[citation needed] He joined the tour of Priscilla, Queen of the Desert in the same month, sharing the role of Tick/Mitzi with Duncan James and Jason Donovan.
[citation needed] In March 2017, Day toured in Grease in the role of Teen Angel, a revival of the show in which he had previously played Danny Zuko.
[citation needed] Currently 2021 touring in Chicago playing lawyer Billy Flynn Darren returned to pantomime in 2022 starring in Peter Pan as Captain Hook at the Regent Theatre, Ipswich In the 1990s, Day was engaged to Anna Friel, Tracy Shaw and Isla Fisher.