Hepburn and Grant in a rom-com (I guess I'm being anachronistic ... I think the term "romcom" didn't become part of the language until the 1970s ... but Holiday is a romantic comedy, so shoot me). Holiday is often compared to The Philadelphia Story, which makes sense. The two films share a common source (both from plays written by Philip Barry), Donald Ogden Stewart worked on both screenplays, George Cukor directed both movies, and they both star Katharine Hepburn and Cary Grant. Holiday didn't fare well in comparison to the later picture, at least at the time. It came near the end of the period when Hepburn was famously considered "box office poison", while The Philadelphia Story ended that reputation. But Holiday is perhaps more highly regarded today, with its theme of how a person should balance their work life with larger considerations.
Holiday is not a screwball comedy, unlike its Hepburn/Grant predecessor Bringing Up Baby. In fact, it's not often very funny at all. At times, it's quite serious. But the playing, the casting, everything feels like a romantic comedy, and it's only after the fact that you realize the subtext was close to the surface. The plot is farce and much as anything ... Grant's self-made man is about to marry Hepburn's sister (they come from a very rich family), but eventually he and Kate realize they were meant for each other. The stars are good, as they usually were, and the support includes Lew Ayres underplaying the role of a drunken brother. Edward Everett Horton is always welcome, and he doesn't fall into his usual schtick here ... in his way, he is quite forceful. You can easily treat Holiday as a straightforward romantic comedy, but it benefits from a consideration of the depths of the two main characters. #943 on the They Shoot Pictures, Don't They list of the top 1000 films of all time.