Like many of the films that the writer-director has made since, Paul Thomas Anderson's debut feature, Hard Eight, is built around human connections that are dramatically premised, at least in part, on clashing emotional or intellectual bandwidths. Anderson using the easily understood language of mentor-mentee relationships here to pick away at his characters, slowly revealing the private motivations that they otherwise keep hidden from each other. John C. Reilly plays John Finnegan, a penniless and presumably homeless gambler, first seen wrapped up in layers of polo shirts and flimsy jackets, spinning yarns about wanting to raise enough money to pay for his mother's funeral. He is approached and treated to cigarettes and a warm cup of coffee by Philip Baker Hall's Sydney, a supernaturally relaxed old timer who takes pity on John, teaching him how to manipulate casino staff into believing you are spending much more money with them than you actually are in order to leverage freebies like comped drinks or an overnight hotel stay.
We then pick up the story years later with Finnegan firmly ensconced in Sydney's rootless racket, living comfortably and attempting to build a connection with Clementine, a flaky cocktail waitress played by Gwyneth Paltrow. Although cold, hard facts are revealed by the film's conclusion, throughout much of Hard Eight the audience is left to wonder about Sydney's motivations regarding this hopeless pair. Both John and Clementine initially suspect their benefactor of harbouring some sexual desire for them, these speculations clearly informed by grim experience, but Sydney dismisses John's harsh invective and Clementine's frozen, nails-in-thigh shock. An aside about Sydney having a daughter and son somewhere, who he clearly is no longer on speaking terms with, seems to be a more accurate insight into this man's intentions and why he spends a significant amount of time orchestrating, for an infantilised, impulsive protégé, situations and outcomes that do not particularly benefit the older man. Quite the contrary, in fact. On release, back in the mid '90s, the obvious disparities in not just presentation but intelligence between John and Sydney likely raised a few irony poisoned chuckles but, with the benefit of Anderson's wider catalogue now in play, this writer-director's inquiries into these mismatched relationships read as sincere, even tragic.

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