The Holdovers - with Oliver

This week we are reviewing the 2023 American Christmas comedy-drama The Holdovers, directed by Alexander Payne, written by David Hemingson, and starring Paul Giamatti, Da'Vine Joy Randolph, and Dominic Sessa.

Set in 1970, the story follows a curmudgeonly classics teacher at a New England boarding school who’s roped into chaperoning a small group of students with nowhere to go over the Christmas break.

We welcome back Oliver to the pod this week — and we set ourselves a goal: try to reduce the Aussie to tears three times during the episode.

We don’t waste any time. The Scotsman opens by asking the Aussie:
"What’s your proudest memory of your son?"
And boom. Straight to the Kleenex. Emotional scenes.

From there, we move into sibling rivalry, before diving into the idea of the “walk of no judgement” — a cleansing or confession-style conversation kids wish they could have without fear or backlash. It’s a surprisingly touching segue into this film.

Oliver calls The Holdovers “a beautiful, beautiful film.”
The Aussie… disagrees.

“Predictable.”
“A poor man’s Dead Poets Society.”

And then Oliver hits back with one of the best comebacks of the episode. You’ll have to tune in for that one.

The Aussie does, however, go full fanboy over Paul Giamatti. Meanwhile, the Scotsman says Giamatti is the only reason he got through the movie. “If he wasn’t in it, I’d have switched it off.”

We get into themes of grief, loneliness, and the warmth of unexpected connection — plus a detour on white Christmases, global warming, and where they intersect. Yes, really.

Oliver also gives a sharp and insightful explanation of why it’s called The Holdovers — even though there’s only one student left behind. It’s a brilliant observation.

Rohan Reminisces returns with the debut of “Guess the Celeb”, which sparks chaos. And just when you think the episode’s wrapping up, the Aussie completely embarrasses himself in the final few minutes — classic ending.

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