
1938 · George Cukor
How Holiday has been received, argued over, and remembered.
It underperformed in 1938 — right in the middle of Hepburn's 'box office poison' era — and was overshadowed for decades by The Philadelphia Story. Now it's the cinephile's pick of the Grant–Hepburn films, Criterion-canonized and routinely called the best thing Cukor, Grant and Hepburn ever did together.
The perennial fight: is Holiday actually better than The Philadelphia Story and Bringing Up Baby — the 'underrated sibling' take that's now so common it's practically the consensus.
Cary Grant's backflips — real, no double, courtesy of his acrobat past — are the film's endlessly gif'd signature, and its New Year's Eve setting has quietly made it a cinephile holiday-season ritual watch.
A canon climber turned Letterboxd darling: the 'trust me, skip the obvious one and watch this' recommendation of 1930s Hollywood.