"When Breath Becomes Air by Paul Kalanithi. Kalanithi’s brave memoir chronicles in exquisite prose his brave battle with terminal illness, but rather than verge into depressing territory, it is a triumphant and inspiring read. His words make one rethink our perception of time—to not only imagine what we might achieve in the future, but to cherish the beauty that surrounds us in the present"

"One of the most gloriously depressing films ever made, an awkward tribute to the dysfunctional family in seventies America. And the wallpaper in many scenes is a tacky sort of perfection. So if you’re in a mood to get pretty bummed out, and look at some really authentic wallpaper, look no further. This film is like getting punched in the stomach with a rotary phone."

"I would say number one is probably Fellini’s La Dolce Vita, which I never get tired of. Even though parts of it are very grim and depressing, I think if there was a movie I would want to live in, it would be that. You know, if the world could be the Trevi Fountain in black and white, with Anita Ekberg holding a kitten on her head."

"I once took a girlfriend to see this movie, after which she complained that it was the most depressing film she’d ever seen. I should’ve known right then and there that our relationship was doomed. It depicts the harsh toll of loneliness, humiliation, and indifference to the suffering of others; what it’s like to live in a world where empathy is in short supply (which is usually the case)."