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TIFF26: The Life and Deaths of Wilson Shedd Asks for Empathy

Courtesy of TIFF

Twenty-seven states in America have the death penalty, although four of them have paused executions due to executive action. Globally, 53 countries allow capital punishment, but 23 of those countries haven’t used it in the last ten years. The death penalty is an issue that has always divided the general public. Proponents of the punishment support it in the abstract, but this debate is about more than nebulous opinions. The Death Penalty Information Center has spent thirty years researching cases and highlighting biases, deaths of innocent people, and other lesser-known truths of the death penalty. Tim Blake Nelson’s 2026 Toronto International Film Festival-premiering movie, The Life and Deaths of Wilson Shedd, is a starkly up-close look at a man on death row and what awaits him.

Told in a non-linear fashion, The Life and Deaths of Wilson Shedd has three main timelines. The oldest is of Wilson Shedd’s (Scoot McNairy) imprisonment, then comes his escape and the family (William Jackson Harper and Devyn Tyler) he encounters, and, finally, the night of his execution. Wilson was arrested and jailed for murder. He’s spending his life in prison, but is considered one of the “better” inmates, which gives him access to a creative writing class taught by Karen (Amanda Seyfried, who wowed TIFF last year with The Testament of Ann Lee). While she may be free and living outside the bars Wilson finds himself behind, Karen is in a prison of her own. Her husband (Grant Harvey) is violent and abusive, but she doesn’t see a way out until Wilson presents her with one. The two are longing for someone to see who they are beyond the circumstances they’re in, and it leads them down a path they cannot return from.

Wilson stands in his cell door in The Life and Deaths of Wilson Shedd.
Scoot McNairy in The Life and Deaths of Wilson Shedd. Image Courtesy of TIFF

Many non-linear films try to find emotional resonance in jumping around in a storyline, with varying degrees of success. The Life and Deaths of Wilson Shedd is an instance where the time jumps actually contribute something to the story. In one of her classes, Karen tells her students that every book, movie, or narrative work has to have a beginning, a middle, and an end. This works when you’re digesting and critiquing something that has these finite beginning and ending points, but life is a lot murkier. One could say that life begins when a person is born and ends when they die, but that’s just not true, is it? The circumstances a person is born into mean their story started long before they did. Similarly, the way they die creates endless ripples going forward. Just as The Life and Deaths of Wilson Shedd has no traditional beats of a story arc, Wilson Shedd’s life had his deck of cards shuffled and dealt before he came to be.

Scoot McNairy is one of those Hollywood guys who’s been around. You’ve seen him in something, even if you can’t place exactly what it was. He’s so much of a chameleon that he disappears into whatever the project asks of him. The Life and Deaths of Wilson Shedd asks him to lead, and he does. His Wilson is charming, and he has to be. The audience has to understand how a woman like Karen, who by all accounts has a steady head on her shoulders, could risk everything for him. In his writing in Karen’s class, there are glimmers of the kind of life he could have had if things had been different, but none of that excuses the violence he unleashes to save his own skin.

Karen talks to Wilson in jail
Amanda Seyfried in The Life and Deaths of Wilson Shedd. Image courtesy of TIFF

Few scenes in movies stick with me the way the last fifteen minutes of The Life and Deaths of Wilson Shedd have. Given the subject matter, it’s easy to guess how this story has to end. Blake Nelson, who also wrote and co-starred in the film, was loosely inspired by true events. He doesn’t cite a particular case that allows him narrative freedom, but he does speak to the fact that there are many instances of executions that didn’t go as planned. McNairy is particularly devastating in this sequence, but so is Missi Pyle in her small role. She plays against type, allowing an underseen dramatic side to come to light.

The Life and Deaths of Wilson Shedd argues that the death penalty should not be looked at in the abstract, but in the deeply human reality it exists in. The film is humanistic and complex, by far one of the more difficult watches of the year. It asks about the role of punishment in society. Who decides it, how it’s carried out, and whether it serves a larger purpose. The Life and Deaths of Wilson Shedd has no answers, merely questions and empathy for all its characters.

Written by Tina Kakadelis

News Editor for Film Obsessive. Movie and pop culture writer. Seen a lot of movies, got a lot of opinions. Let's get Carey Mulligan her Oscar.

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