Oliver Matheson’s review published on Letterboxd:
My great and unexpected love for Bringing Up Baby most likely clouded my expectations for this one, which I assume worked against Holiday’s favor. The two leads may be the same, but two different directors and two different tones can go a long way, and for some reason I forgot about that. Still, the day I regret watching a Cary Grant film is the day I die.
Holiday tells the story of working-class bachelor Johnny Case (Cary Grant) who begins a whirlwind romance with Julia Seton (Doris Nolan) before discovering that she comes from an extremely wealthy banking family. The lives of Julia and her two siblings (Katharine Hepburn and Lew Ayres) are controlled by the head of the family. The impact that this control has on the Seton family is meant to be the emotional core of the film, and unfortunately that just did not connect with me. I think getting the audience to feel bad for insanely rich characters is a tough ask, and it didn’t necessarily work here.
The first act of the film is great though, terrific energy and we get some fun Cary Grant as a fish out of water scenes, but once we settle into the plot it quickly loses steam. So much of the film wanted us to invest in the idea that we should all fall in love with Hepburn’s character and I just… didn’t. You can’t go wrong with seeing actors of this caliber bounce off one another, and a great ending is always helpful, but with no interesting visual style or significant themes this holiday is not as memorable as I had hoped it would be.