The Five Most Gut-Wrenching Documentaries I’ve Ever Seen

Must-see documentaries if you enjoy experiencing some extreme emotions

I am not one to shy away from films or documentaries that are going to make me feel something. In fact, I love when movies, no matter the genre, take me on an emotional rollercoaster. The scarier, sadder, weirder, or sicker, the better.

Of all the documentaries I’ve ever seen (and I like to think I’ve seen far more than the average person), these were by far the ones that affected me the most on an emotional level.

The Act of Killing

Probably my all time favourite documentary. This is the only documentary I’ve ever watched that made me feel like throwing up my popcorn. But I couldn’t turn away. The Act of Killing somehow balances being funny, wildly creative, and fascinating, with being gruesome and terrifying. In a strange way, it gave me hope for humanity by providing the most convincing evidence I’ve seen yet that even people who we write off as evil (or lost causes) still seem to know, however deep down, right from wrong — especially when it comes to taking a human life.

Where to watch: free with Amazon Prime

What He Did:

I don’t know a single other person who has watched this documentary—it only has 23 ratings on IMDB— which I think is such a shame. This is the only screening I’ve been to in which many people walked out of the theatre—presumably because they, like me, felt like the emotional weight of the film was too much to bear. For the first time in my life, I actually understood what it was like to want to self-harm. I remained in the theatre though, and coped by digging my nails as hard as I could into my palms to distract from the psychological pain with some physical. This is an extraordinary story of what it is like to live with deep remorse.

Where to watch: rent or purchase on Vimeo

32 Pills: My Sister’s Suicide

This film was exquisitely made and, in many ways, a touching tribute to a very talented artist (dare I say, one of my favourites now?) who committed suicide before she received appropriate recognition for her work. It helped me see how frustratingly hopeless it is to search for answers when sometimes there are none. It’s enough to drive someone mad, and as you watch that very truth unfold, your sorrow compounds.

Where to watch: free with HBO subscription

Tell Me Who I Am

Warning: this one deals with such grotesque subject matter, that I actually tend to advise against watching it. It’s genuinely haunting, chilling, sickening. It’s literally an unbelievably improbable story, yet it’s true. I was worried I’d have twisted dreams after watching it— thankfully I didn’t. Still, it introduced me to a concept that had never before crossed my mind and I wish never did. If you’re an empath, watch at your own risk.

Where to watch: free with Netflix subscription

Prison in Twelve Landscapes

This documentary, while being troubling and infuriating, did an incredible job exposing the deep and widespread injustices of America’s prison industrial complex. We’re reminded that inmates aren’t the only ones affected and that injustices are seemingly never ending. It’s hard to see a good reason for jailing anyone after you watch this.

Where to watch: rent or purchase through Apple

Note: I generally smoke some weed before watching a documentary, so my feelings end up being extra amplified, and I empathize more deeply with the characters, for better or worse. If you don’t want to feel such extreme emotions as the ones I describe above, I’d recommend not consuming any illicit substances beforehand!

Brooklyn based Start-Up Advisor, Impact Investor, Filmmaker, Writer, and Leadership Coach. I focus my time on the future of learning and the future of work.

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