I didn’t want to see The Holdovers because it looked like a troubled-young-man-comes-of-age story, a genre that bores me (there have been so many). I was persuaded to go by friends, found it was a sad-middle aged-weirdo-man-finds-himself story, and liked it even less.
Now, I think Paul Giamatti is a great actor, but was underwhelmed by the performance. I had no empathy for the character (and I am a veritable fount of fictional empathy), or indeed any of the characters. The manipulative sad teen boy, the saintly suffering middle aged bereaved mother for whom Da'Vine Joy Randolph won an Oscar, the various secondary characters.
I would have been more interested in the movie if it had held on longer to some of the secondary characters. The dynamic among the group of miserable outcast boys was a bit interesting and could have been rewarding, but off they went skiing, Carrie Preston I always enjoy, and the awkwardness of this creepy sad dude thinking she’s into him because she’s sociable and nice could have been fruitful.
The whole movie seemed set up to make me not care, as off-putting as the protagonist with his self-hatred and bad breath.
Personally found the Mary Lamb character made a lot of sense and was pretty sympathetic, not saintly exactly so much as lost. Because she was someone who had built her whole life around sacrificing for her son (working and LIVING at a school almost entirely full of pampered, entitled rich white boys/men would have been lonely as hell, her sister lived pretty far away and got the impression they rarely saw each other, she didn't have her own car, and didn't seem to really have real friends there), made him her world and her purpose, and then he died, senselessly, and all of those years devoted resolutely towards giving him opportunities to achieve his full potential were for what? And what now?
But agree with Amareldys, for the most part I experienced it as one of those comedies that detours into dark, painful places and enjoyed it, despite it very much being focused on a man and a boy veering towards becoming slightly less dysfunctional people. And isn't it funny how much something striking as comedy or not changes EVERYTHING about the experience?
Sounds like she should of been the protagonist of this story and who it revolved around. Powerful stuff, would have been more meaningful.