Despite a talented cast and appealing cinematography, this drama never manages to escape from under its heavy tortured artist/boozy writer world. Moving back and forth between the three timelines manages to keep things somewhat interesting, but The Vanishing of Sidney Hall does so in a heavy-handed enough way that it suggests the story's tragedies before they come together. And there are too many unanswered questions -- "Why didn't they go to the police?" "Why did their relationship fail?" -- to set the story (and viewers) free. Things open promisingly enough, with teen Sidney reading his wildly inappropriate, Philip Roth-style story to his high school English class. But that boldness and wit is mostly talked about from then on, rather than shown. Where 2017's Rebel in the Rye offered a window into an artist's process, Vanishing intentionally keeps us at arm's length. Unfortunately, that means we have to rely on glowing accounts from fans to believe in Sidney's brilliance.
That's an important flaw, considering that Sidney's seminal work is inspired directly by the events of the first timeline. We never really understand his reaction to those events because we never learn the contents of the book. We know it inspires some scary behavior in deranged fans, but that's all. Why is it so powerful? What, in the end, did he say about those events when given the chance to tell the world? And his romance with Melody, clearly intended to be central to his motivations in the film, is given horribly short shrift: We never learn why they're in such dire straits in the second timeline. It's rather like La La Land: If this was the love of their lives, what could tear them apart? Those lingering, serious issues rob Vanishing of its potential power. We're left instead with gloomy-writer clichés (he uses a typewriter, which makes him ... more authentic?; as a teen, he has photos of the likes of Oscar Wilde pinned to his wall; and he drinks, drinks, drinks) rather than an authentic experience. What starts as hopefully a riff on the self-imposed exile of J.D. Salinger or perhaps Syd Barrett unfortunately never leaves the ground.