8 Sad Songs for When You Need a Good Cry

There are times when a song comes out of nowhere, hits you at just the right time, and allows your body to unleash a deluge of emotion that’s been pent up for days, weeks, months, maybe even years. And then there are times when you gotta line up some tracks that will poke that big sad bear until the tears flow and you finally let go of what you’ve been holding onto.

So, since I’m apparently in my sadboi era, why not dig this metaphorical knife in a whole bunch more? I present to you a handful of songs that have hurt me in the best way possible, so maybe they can do the same for you, starting with…

“Don’t Think Twice, It’s Alright” – Kesha

Back in 2012, an album of Bob Dylan cover songs was released, featuring artists like Dave Matthews Band and Sting performing ol’ Bobby’s songs, but it’s Kesha’s cover of “Don’t Think Twice, It’s Alright” that was the standout.

You’ll be hard-pressed to find a more transformative rendition of any song as, over the course of the 3-minute 47-second track, Kesha tearfully sings through the words with little band accompaniment. It’s so painful to listen to because it’s so clear how painful it was for her to sing.

“Walking By” – Something Corporate

On their first ever project, the Audioboxer EP (2001), Something Corporate closed out their piano-driven pop-rock/punk debut with “Waking By,” a desperate plea after lost love.

At the end of the song, frontman Andrew McMahon sings: “What did I do that you can’t seem to want me? And why do we lie here and whisper goodbyes? Where can I go that your pictures won’t haunt me? What makes it so easy for you to be walking by?”

Almost 25 years later, this still absolutely wrecks me every time.

“Breathe Again” – Joy Oladokun

While seemingly about struggling with a crisis of faith, there’s a lot about Joy Oladokun’s 2021 song “Breathe Again” that I feel touches on depression, hopelessness, and struggles with identity. You don’t need to be going through a breakup for this song to peel off the duct tape covering the cracks in your emotional pipes.

“A Father’s Song” – Allen Stone

To be fair, Allen Stone’s “A Father’s Song” isn’t a “sad” song, but it’s a song that can certainly hit you in the gut, and I know this because I recently watched him perform it for a sold out crowd and there was not a single dry eye in the room by the end (but I’ll have more on that in the next couple of weeks…)

In the song, Stone sings his hopes, pains, loves, and regrets to his young children, and he does it with such poised vulnerability. We all have fathers, have lost fathers, are fathers, or never knew our father, and regardless of the nature of your paternal relationship, there’s just no way around it tugging on your heartstrings.

“An Evening I Will Not Forget” – Dermot Kennedy

Dermot Kennedy’s “An Evening I Will Not Forget” is a journey through finding and losing love, but, more specifically, losing love with someone who won’t really be out of your life when it’s all over.

At one point, he sings, “But I still get to see your face, right? And that’s like nothing they can take, right,” and, to me, that’s just so brutal. The idea that they’ll always be there, but it’ll never be the same. Every moment, conversation, and touch will be reduced to an image of them burned into your brain that can’t be taken from you, and that will just have to do.

“Let Go of Me Slowly” – Sekou

Breakups can be so hard, but sometimes it’s the pre-breakup moments that are the most devastating: the recognition that the person you love doesn’t love you back anymore. This is the sentiment in Sekou’s “Let Go of Me Slowly,” which finds him begging, “If you’re letting go, please, let go of me slowly.”

“The Great Divide” – Rebecca Black

In the years after “Friday,” Rebecca Black sought to rise above the way her career started and dropped what I believe is one of the most underrated breakup songs of all time, simply because people unfairly didn’t take her seriously.

The song builds perfectly, has a beautiful melody, and her vocal performance is phenomenal. Lyrically, the track asserts the need to leave a toxic partner, with Black singing, “Wash my hands. Turn my back. I don’t need the memories we have,” and “funny how history ends in an instant.”

If any other big-name pop star had dropped this track back in 2016, the world would have been clamoring for it. I will defend this under-the-radar breakup tearjerker until the day I die.

“I Close My Eyes” – Randy Siitam

Maybe I’m cheating a little here, but this song makes me cry a lot, especially lately. I’m literally crying while I write this. Before I drop it on you, I want to explain myself…

You don’t know Randy, but he was one of my best friends in the world, and he died two weeks ago. Randy was a songwriter who’d been through a lot of loss in his life but somehow always managed to come out on the other side with his inexplicable and infectious hope intact. It’s cheesy, and he’d hate it, but in conversations about seeing the grey of life in between black and white, I like to say that Randy saw color.

Not a ton of his music made it online, ’cause he never really had a big break, but Randy did upload a few songs to ReverbNation a while back, and this song, “I Close My Eyes,” is one that’s been on repeat for me.

It isn’t necessarily sad, but it does deal with loss. “Somewhere you got lost on a page I couldn’t find,” Randy sings at the beginning, but what’s so captivating about it is how he turns the grief into hope, going on to sing, “Even through the darkness, I can see your face, every time I close my eyes.”

There’s also just something about the bareness of the recording. It makes me feel closer to him, and that makes me cry. It’s fuckin’ sad, man, but it’s also really beautiful.

Randy, I love you, and I’m sorry that I didn’t do more to share your gift with the world while you were still alive. I know you’re watching from somewhere out there in the universe, and you’re really happy to be making so many people cry.