the best of the sad

I’ve been thinking a lot about the types of stories I enjoy, from books to movies to television. In the last week or so, after various conversations with friends, I’ve decided to come clean with the fact that my taste in fiction generally leans toward the dark and depressing. It’s easy to get stuck in a rut, so I try to read widely, which includes books with a lighter premise or tone. But the truth is, I feel much more at-home with stories that explore the uglier sides of society because I find it fascinating to see how people (fictional or not) deal with their problems.

(This is not to say that I enjoy scary movies. I do not. At all. Someday, I will tell you all about how watching Gremlins in the movie theater as a five-year-old pretty much ruined my life. Or how the scene I deem most frightening in The Shining is hardly the scariest at all.)

But I have found that it’s easier for me to reread darker books than it is to rewatch darker movies or television series. (Seriously, Six Feet Under, I heart you so hard and think about you all the time, but I’m not sure I can ever watch you again. I’m still destroyed by your series finale, seven years later.) Which made me realize, there’s a good amount of movies that I loved to pieces, but I honestly don’t think I can ever watch again. After some serious reflection [i.e., perusing my Netflix ratings], here are my top four:


I have my issues with certain Disney movies (doesn’t everyone?), but there is something about their very old animated films that never fail to bring me back to my childhood. They are some of the first movies I remember watching over and over again, and my mother is a huge fan, so we always had them around the house. But Dumbo? Nuh-uh. Most people point to Bambi as The Saddest Disney Film Ever, but have you watched Dumbo as an adult? He’s relentlessly mocked because of his ears, has one friend, AND IS TAKEN AWAY FROM HIS MOTHER WHO IS CAGED IN ANIMAL PRISON. Sad elephants + circuses + that horrifically depressing Baby Mine song? Apparently the movie is only 64 minutes, but that’s an hour and four minutes that will never again receive my tears.

The Squid and the Whale

Well, this one was unexpected. I think I initially watched because I’m a fan of Laura Linney, but I didn’t expect to sob my way through. It’s about divorce. It’s an uncomfortably intimate view of a family dealing with divorce. Which, if you’re a child of divorce, it can resonate in a way that is wholly unique and heartbreaking. It’s an incredibly well-done movie (and also quite funny at some parts), but it took me a few days to get over this one and I imagine it wouldn’t be any better the second time around.


To be fair, I have seen E.T. more than once. I was only three years old when it was first released, but I very likely saw it in the theater since a) my family liked going to the movies, and b) I had an older brother who was nine at the time. I decided to rent it several years later, when I was in junior high and you know what I decided? Never. Again. That music. That friendship. And the goodbye at the end? It all adds up to me in a puddle of tears and dude. I just can’t.

Boys Don’t Cry

I saw this movie a few years after Hillary Swank won the Oscar, but I couldn’t help wishing I’d seen it before her win so I could cheer her on for such a moving (not to mention deserving) performance. I think I spent the majority of the film holding my breath. And the next three days or so hating humanity. Out of all the movies I’ve mentioned, I think it’s probably the most difficult to watch. Let’s be clear: it’s not enjoyable. But it’s an important story and one I think everyone needs to watch.

Do you rewatch movies that sent you into the depths of despair? Which ones would go on your list?