Hi, {{first_name | friend}}! Welcome back to Worth the Watch. As the weather changes and those of us who suffer from the winter blues start to feel the effects of dwindling Vitamin D, now’s the perfect time to watch something melancholic and moody. Inspired by Meredith’s 5 hidden gem romances with cozy fall vibes, I’m using today’s Worth the Watch to dive deep into the one genre I’m a certified expert on—sad boy cinema. Keep reading for my under-the-radar picks that deserve a spot on your watchlist this fall.

Before we jump in, I have an exciting update: The next film for our monthly Worth the Watch movie club is… Home for the Holidays! This 1995 Thanksgiving family dramedy starring Holly Hunter and Robert Downey Jr. is a hidden gem in the truest sense of the word (only 26k people have logged it as watched on Letterboxd). As a completionist eager to watch all of RDJ’s filmography and a fan of discovering under-the-radar movies that most people have never seen, I can’t wait to cover this one! To join in on the fun, watch Home for the Holidays (streaming free on YouTube!) before the movie club email hits your inbox on Friday, November 6.

Now, let’s get into it. Below are 5 sad boy movies and shows that are absolutely worth a watch (and your tears).

Sad boy rating: 🥀 🥀 🥀 🥀 🥀

Back in my peak sad boy era, I would seek out movies that were an emotional gut punch. For whatever reason, movies that captured the most heartbreaking, depressing aspects of the human condition were also the movies that made me feel the most connected to life. Sad stories have always been oddly life-affirming to me.

This cosmic, tragic fantasy takes a classic piece of wisdom—loving and being loved by someone is always worth it, despite the pain—and repackages it in a modern, fantastical way with the old-school A24 aesthetic. In other words, it’s a masterpiece. The film stars Rooney Mara and Casey Affleck, but their faces are rarely even on screen. And yet, you feel so deeply for their characters, which is a testament to David Lowery's remarkable filmmaking.

Also, I’m not usually one to listen to film soundtracks in my free time, but “I Get Overwhelmed” by Dark Rooms from A Ghost Story is still in my Spotify rotation to this day.

—Vanity Fair

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