There are troubling questions posed in Tim Blake Nelson’s effectively glum prison drama The Life and Deaths of Wilson Shedd, a film that will rank among the most overwhelmingly feel-awful experiences of this year’s Toronto film festival. It’s a story told in a disarmingly folksy manner with plucked guitar strings and down south homespun wisdom before it quietly reveals itself to be about something far more serious and startling, elements of an escape thriller but mostly an unsettling moral drama. It’s likely to upset and enrage some but even those who might feel offended will at least feel something, a quality not to be sniffed at during a festival that can often pick politeness over provocation.
It’s the new film from actor turned writer-director Nelson, whose work has often tended to confront and dissect difficult issues. He went to Auschwitz in The Grey Zone, transported Shakespearean tragedy to high school in O, and handled both rape and suicide in his debut Eye of God. It’s a fine line between grimness for the sake of grimness and being unwilling to shy away from grimness, and at times I wondered whether I was being overly prodded, whether certain scenes were bordering on exploitative. I left rattled by what I’d seen and what I was being forced to reckon with, but I think Nelson just about justifies himself and how far he goes partly because he does, in crucial moments, avoid showing more than is needed.
As the film starts, we’re made to moor ourselves, figuring out what it is that we’re seeing and when it’s taking place. There’s Karen (Amanda Seyfried, continuing her recent resurgence), who is starting work at a local prison, teaching creative writing to inmates. One of these is convicted murderer Wilson (a suitably slippery Scoot McNairy), who tries to protect her from inevitable sexist jibes while rapidly developing deeper feelings for her. Even though she’s warned (“If they weren’t all liars, they wouldn’t be here”), the feelings are soon reciprocated, Wilson’s romantic notes an escape from the violence of her alcoholic husband, whom she has recently left for the refuge of her closest friend (recent Oscar nominee Wunmi Mosaku). We also see Wilson in a different timeline, having broken out of prison, trying to hide amid the shadows, in a path that hurtles him toward a new kind of violence. Then there’s an execution taking place, revealed to us in unsparing detail.
There are major narrative leaps to be made here that Nelson can’t quite nail. Despite being loosely inspired by a true story, Karen’s decision to go all in with Wilson, to risk everything including her freedom, is a considerable hill to climb, and despite Seyfried’s gutsy, glamour-free performance (she makes a far more convincing prison teacher than she does a Philly beat cop) and a late-stage scene slightly fleshing out her tough childhood, there’s not enough to get us there. She’s an increasingly fascinating and surprising character to watch, though, once we get over that hump, one who we can’t quite figure out, and the darting timeline, for once not used as a gimmick, shows the impact of her decisions in an intriguing way, questioning our loyalty to who she is and our sympathy to what she might be going through. Much of the film asks us to question the limits of our empathy and what we might be willing to forgive and why (a strand involving a warm, religious family, led by a father played by William Jackson Harper, vocalises the idea that forgiveness is inherently selfish). Something shocking happens about midway through, casting an even darker shadow over the film, and once we understand where this takes the characters, it leads to an uncomfortable dilemma.
It’s impossible to truly detail the whys here without revealing the exact whats but with the film telling us early on that we are grimly marching toward an execution, it’s clear that Nelson, partly inspired by Dead Man Walking, is asking us to consider the complicated ethics of how we choose to punish and why. The finale is deeply upsetting not just for how viscerally unpleasant it is but because of how it makes us study the depths of our own bloodlust and desire for comeuppance after what we are made to watch. Nothing is easy here, and I wonder whether the film’s hard edges might make it a too tricky sell for buyers (it’s as yet without distribution), but I appreciated how odd and uncompromising it all was, a descent into darkness that refuses to guide us back to the light.
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The Life and Deaths of Wilson Shedd is premiering at the Toronto film festival and is seeking distribution

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