Musicals had long been a feature of the CFT repertory but only in the early 2000s did they become a regular component of the Festival season. In 2001, Loveday Ingram directed the 'lost' Gershwin musical, My One and Only, starring Janie Dee and Tim Flavin. Choreography was by Craig Revel Horwood, who was given special mention by critics.

In 2022 CFT celebrated its 60th season with another Gershwin musical (rewritten by Ken Ludwig): the eagerly anticipated revival of Crazy for You, directed and choreographed by Broadway royalty Susan Stroman. The production saw the return of much-loved performer Charlie Stemp, who made his CFT debut in Half a Sixpence in 2016.