George Cukor directed Cary Grant and Katherine Hepburn in their first film together, Sylvia Scarlett, which was neither critically nor commercially successful. Holiday, Cukor's second film with Grant and Hepburn, also failed at the box-office, perhaps because audiences during the Great Depression could hardly relate to the central character's dream of retiring comfortably at thirty.
Grant plays Johnny, who is introduced to his fiancee Julia's rich father Edward, alcoholic brother Ned, and liberated sister Linda. Julia, played by the forgettable Doris Nolan, is never more than a supporting role; she is marginalised as soon as Johnny meets Linda, a typically assertive, charismatic Hepburn character. Our attitudes towards the characters shift during the course of the film: Julia, apparently infatuated with Johnny, initially appears sympathetic, while Ned seems insensitive and irresponsible; later, we are shown the harder side of Julia and the softer side of Ned.
'Screwball' comedies often featured fast, overlapping dialogue, pioneered by Howard Hawks who directed Grant and Hepburn in the excellent Bringing Up Baby. Holiday has its share of rapid repartee, especially when Johnny visits his friends the Potters and when Linda organises a playroom party. Adding to the occasionally manic atmosphere, Grant (who was a circus performer before he went to Hollywood) performs acrobatic stunts, and the Potters present a Punch and Judy show. Other sequences, involving Edward and his aristocratic social circle, are more restrained, with the comedy provided by the snobbish and hypocritical opinions expressed.
Cukor's The Philadelphia Story, also starring Grant and Hepburn, is lighter and more romantic. Holiday, however, particularly because of Linda's passionate rejection of protocol and privilege, seems a more significant film. Holiday was based on a play by Philip Barry, who also wrote The Philadelphia Story; the play was first adapted by Edward H Griffith in 1930, and Edward Everett Horton played the same role (Edward) in both film versions.