These three songs from Taylor's Swift album Fearless always make me start crying. I have a few of the lyrics in italics under the title. 

You're not Sorry 

You're not sorry, anymore. I won't pick up the phone, this is the last time. I won't hurt anymore. You can tell me that you're sorry but I won't believe you baby like I did, before. You're not sorry. 

Breathe

And I can't breathe, without you but I have to breathe.... it's two a.m, feeling like I just lost a friend, hoping you know it's not easy, easy for me.

White Horse

Say you're sorry, that face of an angel comes out just when you need it to. As I pace back and forth all this time, 'cause I honestly believed in you. Holdin' on, the days drag on, stupid girl. I should've known. I should've known. That I'm not your princess, this ain't our fairytale, I'm not the one you'll sweep off her feet, lead her up the stairwell. This ain't Hollywood, this is a small town. I was a dreamer before you came and let me down.  

Ok, the song Pompeii makes me so so sad! I love it, it's a great song, but whenever I hear it I just can't stop thinking about all the poor people in the actual Pompeii who were buried alive. I don't know. I just get chills listening to the song. It's weird.

Who Lives, Who Dies, Who Tells Your Story

"she's buried in Trinity Church near you, when I needed her most she was right on time"

Only ONE book has ever made me cry. And it took me a while to realize that the charrie died. 

SPOILERS

Although I soon discovered she didn't. XD 

DX t'ndid ehs derevocsid noos I hguohtlA .koob s'lireP ni yrolG

~~~

That's all. :)

Although hopping back and forth between charries perspectives will make me cry if the charrie is really upset.

Oooh... Who lives, Who Dies, Who tells your stories, definetly, and Stay Alive reprise, and The World Was Wide Enough absolutely terrifies me, and... all the songs in Hamilton where people die :(

Also Sonny's part in Carnaval del Barrio in In the Heights. "...They're selling the dispatch and they're closing the salon, and they'll never turn the lights back on, and we are powerless, we are powerless, and y'all keep dancing and singing and celebrating, and it's getting late and this place's disintegrating, and we are powerless we are powerless..." And the song Alabanza from the same musical.

Also some songs randomly make me feel this weird sense of dread like the world's about to end. I don't know why or what any of them are called. It's strange. 

"It's Quiet Uptown" from guess what? Hamilton! Is one of those songs that can make me start tearing up. As well as "Dear Theodosia." *sniff* Also, "Two Birds" is a melancholy song for me.

You know, art making you feel something is called "catharis". We were talking about it in English class.  

Hmm . . . I can't think of anything that's exactly depressing, but one book close to it was The Book Thief (I wasn't fond of it just because of that, I thought it was a little long and boring). 

Some books make me cry. I was really sad with one book, and another series made me cry a lot. 

SPOILER ALERT

One book that made me cry was Plain Kate when Taggle died! But he didn't die forever so that was good.

And another series that made me cry was the Anne of Green Gables series when (names backwards) wehttaM (In the first book), ecyoJ (House of dreams), and, most of all, retlaW!!!! (SO SAD) And when ybuR died it was sad, too, but not as sad, because we didn't know her that well. Still sad. 

SPOILER ENDS

I don't really know any songs that make me cry, though. 

West Side story. Oh man, how excited they are in the begining, when they've got their whole lives ahead of them, and their young and in love, and then. . . Also all the sad songs in Hamilton. I'm listening to It's Quiet Up Town right now. It's really hard to keep from crying. Oh Philip! 

Yay! More Hamilton fans!

My mom made me watch Me, Earl, and the dying girl

It is SO sad. Not recommended for sentimental people/ people with hearts 

Some songs that make me sad/nostalgic include: 

The Kids Aren't Alright by Fall Out Boy (specifically the bridge at the end. Sometimes it makes me happy, sometimes it makes me sad)

Addict With a Pen by Twenty One Pilots 

Trouble by Halsey

Goner by Twenty One Pilots

Stone Cold by Demi Lovato

You Found Me by The Fray

Love is a Laserquest by Arctic Monkeys

And probably a lot more that I can't remember. One book that really touched me was Will Grayson, Will Grayson by John Green (Warning: it is really innapropriate! Ask your parents if you decide to read it!) It was just so... i don't know, not sugarcoated like a lot of books are. Up made me cry, and so did Inside Out (I'm really emotional, okay?) Also, one of my hobbies is looking up sad short films to make myself cry. Some good ones that are appropriate are ReMoved and Remember My Story (it is a sequel to ReMoved). I definitely recommend those! Another thing for PJO/HOH fans- Viria (a popular fanartist in the PJO world) did two song thingys with fanart for each line of the songs Let's See How Far We've Come by Matchbox Twenty and C'mon by Panic! At the Disco and fun. They are so cool and touching!

I watched a series of short films recently that were really depressing and thought-provoking, but unfortunately there's a few swears, inappropriate topics, and a small amount of violence, so I probably shouldn't say the titles.

Other than that, there are very few songs, books, or movies (yes, even hamilton) that have ever made me overly sad. The only one that I can think of is If You Could See Me Now by The Script. I'm not really a fan of most of their music, but I admit I got a lump in my throat after hearing the story behind it.