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It's curious how powerfully movies – the medium that put the "mass" in entertainment – speak to us about loneliness.

Three viewing experiences – Lonesome, The Game and Herman's House, brought this home again recently, movies otherwise so completely distinct you'd never accuse them of having anything in common.

But look again: Lonesome is an exquisite 1928 part-talkie about a working- class man and woman (Glenn Tryon and Barbara Kent) who find and lose each other on Coney Island one perfect afternoon; The Game, David Fincher's 1997 movie about a misanthropic multimillionaire (a custom-cast Michael Douglas) who learns what it's like to be really alone when his world is transformed into a full-blown film-noir nightmare; and Herman's House, Angad Singh Bhalla's hugely moving documentary about a man shut in solitary confinement for 40 years and the virtual home he builds over the phone with the help of a New York artist.

That I watched all of these alone in my home – the first two are new Criterion Collection home disc releases, and the third was provided in advance of its opening this Friday night at the Bloor Cinema – merely delivered the message that much more forcefully: We live alone against nature.

Lonesome, only recently reclaimed as a lost classic of the twilight era linking silent and sound movies, was directed by the Hungarian-born doctor and anthropologist Paul Fejos, a man who eventually walked away from filmmaking when he realized his interests in matters like humanism, regular working folk and making art movies weren't widely shared in Hollywood.

But before he departed to embark on a career as an ethnographic documentarist and respected anthropologist, Fejos made Lonesome, a bewitchingly vibrant and imaginative account of two people lost in New York who come together during the Fourth of July chaos of Coney Island. On the one hand a dead simple love story, Lonesome is also an exercise in cautionary proletarian humanism: Our cities strand us alone in our labour and desperation, and keep us from connecting as anything other than cogs in the larger machine. Small wonder Fejos ultimately gave up on Hollywood altogether.

Although David Fincher, director of Se7en, Fight Club and The Girl with the Dragon Tattoo, might not be the first person who comes to mind when the terms "Hollywood" and "humanism" are joined, it's increasingly apparent that this director is a far more complicated and morally engaged filmmaker than previously thought.

If movies like Zodiac, The Curious Case of Benjamin Button and The Social Network reflect a new genre of film increasingly engaged with the agony of becoming disconnected from our social, familial and romantic moorings, it now seems like The Game was their predecessor. When the smugly self-isolated investment banker Nicholas Van Orton (Douglas) finds himself unnervingly plunged into an all-too-real "virtual reality" game given to him as a birthday present, he's also pushed to the logical extreme of his own misanthropy. It's Scrooge's saga repurposed for the One Per Cent, and a prescient full decade before the crash.

But Van Orton's through-the-looking-glass nightmare is nothing compared to Herman Wallace's real-as-steel one, which began when the New Orleans teenager was convicted on bank-robbery charges and, some years later, sent to solitary confinement for the murder of a prison guard which Wallace has spent 40 years claiming he did not commit.

His transformation into a tragic symbol of the inhumanity of solitary confinement and the racial inequity of the American penitentiary system (Wallace was a founder of the prison Black Panther chapter) has done nothing to spring him from his six-by-nine-foot cell.

Yet how serene he seems, at least judging by the numerous phone conversations we hear him engage in with Jackie Sumell, the former art student who initiated a several year correspondence with the inmate by wondering just what kind of home a man who lives in solitary confinement imagines. Thus began not only a remarkable correspondence but a five-year art project – wherein Sumell built a model according to Wallace's specifications and toured it to 12 galleries in various countries – but eventually a campaign to construct "Herman's House" as a drop-in centre for kids and potential headquarters for progressive penal reform.

That the last development still hadn't happened by the time Herman's House (the documentary) was finished – indeed, Wallace was returned to solitary last year after eight months – is so heartbreaking has nothing to do with whether you think the man is guilty of the charge. It's heartbreaking because the voice you hear, the spirit behind it, and the make-believe house it so vividly imagines living in, reminds you of something movies have been telling us all along: Hell is being left alone.

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