Every now and again, I toy with the idea of creating a playlist entirely filled with songs that leave me emotionally compromised. I look at it as sort of a cleansing experience or as a way to help get good and emotional for a LARP. Also, sometimes you’re just feeling masochistic and need a good cry. That might just be me. Anyway! Today’s list would be some of what I’d put on that playlist. Some of these songs are just really sad and others are contextually sad for me. You’re welcome for the cute (but sad) puppy in the header. I think we’re going to need it.

 

11. “Sandy Hook: Somewhere Over the Rainbow” – The Children of Newtown feat. Ingrid Michaelson

Oof. Yeah. I’m starting the list like this. After the Sandy Hook Massacre in Newtown, CT, indie darling Ingrid Michaelson got together with students from the school to record their own version of the Oz classic “Somewhere Over the Rainbow.” Proceeds from the sale of the single went to help those affected by the tragedy. Tying that event in with these sweet voices just. . .yeah. Tears.

 

10. “Very Good Advice” – Kathryn Beaumont

This song has been my anthem more times than I care to admit. Sometimes, I’m so great with telling myself to do stuff like going to bed at a reasonable time, but not so great with the follow through. Regardless, Alice breaking down into tears during this song just gets me every time. Every. Damn. Time.

 

9. “Into the West” – Annie Lennox

Funny thing. I started typing up stuff for this list while listening to all of my Van Canto collection on my iPod and as I got here, their cover of “Into the West” came on. It’s a good cover and there are a lot of good covers, but there’s just something magical about the way Annie Lennox sings this bittersweet song about death. It was first played at the funeral of a friend of the filmmakers of The Lord of the Rings trilogy. It’s beautiful and oh so sad.

 

8. “When Love is Gone” – Meredith Braun feat. Michael Caine

I’m not going to lie. Old Man Crying is totally my Kryptonite. When Michael Caine jumps in at the end of this depressing-as-all-get-out break-up song, I have to dab my eyes. It’s rough and heart-breaking. This song was cut out of  the theatrical release of The Muppet Christmas Carol for being so damned depressing and for slowing the pace of the film down. That’s just extra tragic.

 

7. “Hurt” – Johnny Cash

This appears on a lot of lists as one of the covers of a song that is so much better than the original. The best thing about this song is that you can really feel the regret rolling off of Johnny Cash’s tongue. This is a man who has been through so much and is reflecting on his life and choices. It’s rough.

 

6. “Say Something” – A Great Big World feat. Christina Aguilera

Oh man. This song. It’s been all over the place for the past few months and with good reason. There are even videos on YouTube of kids bawling while listening to it. I don’t blame them. It’s simple and beautiful. It’s about letting go and it makes me sniffly when it comes up on my iPod. I have to listen to it all the way through, though. It just hurts so good.

 

5. “Dryad’s Promise” – SJ Tucker

I remember seeing SJ Tucker perform this song live. The way she told it, it’s a song inspired by all of the trees that were cut down to make great naval vessels. What about the Dryads that called those trees home? What happened to them? What if they stuck with their trees to the bitter end? Yeah. That’s the song. Sniff. Those poor Dryads.

 

4. “Who Wants to Live Forever?” – Queen

I grew up watching “Highlander: The Series.” I’ve watched the original movie more times than I can count. This song always came up to show the loss of someone near and dear to the hearts of the characters and the audience. On top of that, it’s so beautiful and sad. It really makes immortality seem like such a bummer.

 

3. “Baby Mine” – Betty Noyes

This song always wrecks me. All Dumbo wants is a quality snuggle with his wrongly-imprisoned mother. They show you scenes of all of the animal mothers and their young and then there’s Mrs. Jumbo reaching through the bars with her trunk and cradling Dumbo and. . .I can’t. I just can’t. I need a moment.

 

2. “Back in the High Life Again” – Warren Zevon

Okay. I was in this campaign LARP for a couple of years called Threads of Damocles. At what was slated to be the original game finale (the game went on for a few years after that), a friend of mine made a mix CD inspired by the events and characters in the game and handed a copy out to all of the players. The last song on the CD Warren Zevon’s cover of “Back in the High Life Again.” It’s a downtempo and melancholy cover of the Steve Winwood original. It’s also on the last album Zevon recorded before his death. It really felt like saying “good-bye” to some dear friends and listening to it still makes me weepy to this day.

 

1. “A Boy and His Frog” – Tom Smith

If I need to get weepy for a LARP, I pull this song up. If I feel like coming down a few mood notches, I listen to this song. It’s by renowned filk artist Tom Smith and is all about how Kermit the Frog is supposed to continue after the loss of Jim Henson. Goodness. Typing about this song is making me misty-eyed. So, I’m just going to leave this here because I think I’m going to need some cheering up.