11 Songs Where the Sadness is Legit | Playlist 🎧

“11 Songs Where the Sadness is Legit” features ‘sad’ songs courtesy of ILLENIUM, Khalid, Lauv, Myylo, and XXXTENTACION among others.

“He’s got the fire and he walks with it / He’s got the fire and he talks with it,” Lana Del Rey sings on the chorus of “Sad Girl,” a gem from her 2014 album, Ultraviolence.  Del Rey, who is awesome at writing and singing depressed songs, continues, “His Bonnie on the side, Bonnie on the side / Makes me a sad, sad girl.” Fitting the tone of this particular record is a slow tempo and a minor key.  Honestly, it’s the perfect way to preface 11 SONGS WHERE THE SADNESS IS LEGIT, where the word sad must be featured in some form or fashion in the song title.

Ultimately, 11 SONGS WHERE THE SADNESS IS LEGIT – a list that just touches the tip of the iceberg of sad songs – features songs courtesy of ILLENIUM (“Sad Songs” with Said the Sky featuring Annika Wells), Khalid (“Another Sad Love Song”), Lauv (“Sad Forever”), Myylo (“Sad Boys”), and XXXTENTACION (“SAD!”).  Without further ado, let’s get really, really SAD!  

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1. Lauv, “Sad Forever”

~how I’m feeling~ • Lauv / AWAL • 2020

Lauv (Ari Leff) brilliantly tackles mental health issues on “Sad Forever”, one of many singles released in 2019 appear on his 2020 debut studio album, ~how I’m feeling~. ~how I’m feeling~ follows up the pop musician’s playlist album, I met you when I was 18., which featured gems including “I Like Me Better” and “Paris in the Rain”.

Focusing on the song at hand, “Sad Forever” is produced by Lauv and Halatrax.  Interestingly, it’s a mix of a singer/songwriter vibe with some modern pop cues.  Clearly, Leff wants to invite the listener into the anxiety and depression issues he was facing, maybe even more so than preceding single “Drugs & The Internet”.  On the first verse, he sets up the turbulence he’s experienced, asserting, “Whispers in the nighttime / Voices always keeping me up / Telling me that I should give up.” One of the most beautiful moments occurs on the pre-chorus, as Leff sings, “‘Cause lately I’ve been in the backseat to my own life / Trying to take control, but I don’t know how to.”  On the chorus, he is resolute – determined, essentially, not to let sadness weigh him down and destroy him. On the second verse, he looks ahead, more positively:

“I’m coming through to the other side
I’ll make it through to tomorrow
‘Cause that’s all I can do today, do today.”

What stands out about “Sad Forever” is the resolve shown by the artist.  Also, his falsetto is pretty sweet on the chorus.  Worth noting, I personally included “Sad Forever” on a playlist I curate, Music to Atone to.

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2. Myylo, “Sad Boys”

Sad Boys [Single] • Myylo • 2019

“Hug all the sad boys / Chilling in their Gucci sweaters / Shrug off the sad boy / You won’t feel this way forever.” Talented LGBTQ pop singer/songwriter Myylo highlights the often-neglected topic of male sadness on his succinct but thoughtful, must-hear single, “Sad Boys”. The lo-fi record not only tackles depression, but explores the way that masculinity allows or doesn’t allow men to deal with sadness.

Compared to some of Myylo’s previous singles (bop “Jonesing” from I’m a Nice Boy comes to mind), “Sad Boys” is more low-key when it comes to sound, with more emphasis on the lyrical content, mood, and theme.  That’s a pro, because Myylo has so much to say, beginning with the chromosomal reference of the first verse, to expressing sadness as men, something society so often frowns upon:

“But all my friends never get to say
We’re blue with grief
We’re thinking deep thoughts
We’re thinking deep thoughts like you woulda woulda not
Believe oo-ee believe me.”

Myylo offers solutions as well as more of the mindset on the second verse (or section if you will) of “Sad Boys.” The pop singer seems to mention about the importance of support for males going through a variety of issues that cause depression.  Adding to the characterization of “Sad Boys,” it’s also a counterpoint to dads who tell their kids to “man up” and a culture that frequently proclaims that “crying is for girls.”  Myylo offer some specific insight about the single, which makes the messaging even more potent:

“I remember being in literal shambles over getting bullied as a kid. Intuitively, I pushed those feelings down or hid my tears and never told my parents about what I was going through. Looking back, I think that was a gut response to all the ways society teaches boys not to feel. ‘Sad Boys’ is me trying to carve out a little space for boys to be sad or cry if they need to. Tears are tight. Emotions are lit. And, guess what, boys need to make space for themselves to feel them.”

“Sad Boys” is a deep, must-hear single that does a superb job of tackling a topic that seems to be ‘swept under the rug.’ Society needs to progress, particularly when it comes to masculinity.  Myylo provides ‘food for thought’ for the world, and we all seriously need to devour it.

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3. Jonas Brothers, “Happy When I’m Sad”

Happiness Begins • Jonas Brothers / Republic • 2019

Pop bro trio Jonas Brothers shocked the world by making a comeback in 2019 with Happiness Begins.  Prior to the release of Happiness, it had been a decade since a new Jonas Brothers album materialized! Arguably, Nick, Joe, and Kevin Jonas sound better than they’ve ever sounded on the brothers’ fifth studio album.  Fitting the ‘sad’ parameters of this particular playlist, “Happy When I’m Sad” appears as the ninth track on Happiness Begins.

“Crying over old loves even though they’re over / Never gonna stay friends, yeah, stay friends…” Okay Joe, okay! “Happy When I’m Sad” finds Joe Jonas taking over lead on the verses, showing off deeper vocals compared to his younger bro, who often takes the reins during Happiness Begins.  Joe continues to ‘rule the roost’ on the second verse, as he further highlights the contradiction of the two emotions and of course, the perception of others: “See me in the mirror, nothin’ ever changes / Never see the sunset, only in my head.” Nick Jonas drops falsetto on the repetitive, but infectious chorus: “They think I’m happy / They think I’m happy when I’m sad…” Notably, Nick also delivers the bridge:

“I put on a smile, don’t need a face-lift
Why can’t I when everybody fakes it?
Well, they think I’m happy
Like they know exactly how I feel
It ain’t real, but they still think.”

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4. ILLENIUM & Said the Sky, “Sad Songs”

With Annika Wells

ASCEND • Nick Miller / UMG Recordings, Inc. • 2019

“Told me I shouldn’t watch / Got in your car, then we were nothing / All the nights in your room, shit we got through / Left in your dust, yeah.” Hmm, Annika Wells, sounds like matters of the heart to me – heartache and heartbreak.  These matters of the heart go down on “Sad Songs,” which appears as the 12^th song on ASCEND, the third studio album by DJ/producer, ILLENIUM (Nicholas D. Miller). In addition to tapping Wells for vocals on this most sad song, Miller also collaborates with another electronic music producer, Said the Sky.

The majority of “Sad Songs” doesn’t sound like a dance or an electronic pop record.  Annika Wells delivers beautiful vocals throughout, particularly as she hits her highest notes.  Even in her upper register, Wells sings with ease, approaching “Sad Songs” as more of a pop song in a singer/songwriter style. The production of ILLENIUM and Said the Sky reflects this, with guitars appearing in place of bursting, colorful synths and heavy drum programming, initially.  On the memorable chorus, Wells sings:

“Someday I’ll come home
And feel like no one’s even gone
Play this at my shows
And know that I’ve been moving on
Someday I’ll go to bed and I’ll forget I’m lyin’ in your spot
But until some day comes
I’ll be writing sad songs.”

This is an electronic pop record, though it doesn’t occur until late.  Following the bridge where Wells asserts, “Hoo, hoo / I’ll be writing sad songs,” the long-anticipated drop arrives, in all its electronic glory.  This former singer/songwriter-oriented record adds drum programming and most importantly – wait for it – SYNTHS.  Even with greater dynamics and additional instrumentation, Wells continues to write “Sad Songs” on the final iteration of the aforementioned chorus.

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5. Lykke Li, “so sad so sexy”

So sad so sexy • RCA • 2018

Following a four-year hiatus (I Never Learn, 2014), Swedish alt-pop singer/songwriter Lykke Li returned to action in 2018 with , so sad so sexy.  Her fourth studio album ended up being a tight, 10-track affair, clocking in at a mere 34 minutes.  Even with its brevity, so sad so sexy is pretty sweet, including its title track, “so sad so sexy.” “So sad so sexy” is a gorgeous ballad. In the context of the album, it features one of the stronger choruses: “I was only lyin’ when I looked in your eyes / I’m cryin’ diamonds like a river inside / And it’s so sad, so sexy / So sad, so sexy.”

Lyyke Li sings with great expressiveness, exhibiting top-notch musicianship.  Of course, backtracking a bit, she’s not the least bit shabby on the verses either, as she exits the relationship. “Open your eyes, I’m right in front of you,” she sings on the first verse, later adding, “I’m walking out on you for the last time.” Well damn! The second verse is equally short and pretty straightforward: “Don’t turn around / I’m not the one for you / Don’t turn around.”  The end of love definitely contributes to the sadness, where apparently, “Our love was a slow dance / … I dance, but I don’t feel it.” Fair enough.

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6. The Neighbourhood, “Sadderdaze”

Hard to Imagine The Neighbourhood Ever Changing • Columbia • 2018

“Even as a child everyone would say / He was gonna be a star someday / Finally he found a way to reach the sky / But he didn’t know what he’d find.” Those lyrics certainly make you think.  After releasing two five-song EPs – Hard (2017) and To Imagine (2018) – The Neighbourhood, led by Jesse Rutherford, returned with their third full-length album, The Neighbourhood. “Sadderdaze,” a song which concluded the Hard EP, is reprised on The Neighbourhood, as well as its expanded version, Hard to Imagine The Neighbourhood Ever Changing.

The neatest aspect of “Sadderdaze” is by far the wordplay, particularly its relevance to the message. Rutherford discusses the effects of success, particularly within the music industry, yet despite success, he’s still unprotected from “sadder days.”

“Saturdays are not the same as they used to be
Sadder days, why do they keep on using me?
They keep on using me.”

“Sadderdaze” previously appeared on the playlists 14 Songs Where Musicians Are ‘In Their Feelings’, 11 Uniquely-Titled, Interesting Songs from 2018, and 11 Utterly Fantastic Songs About Saturday.

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7. Kacey Musgraves, “Happy & Sad”

Golden Hour • MCA Nashville • 2018

“And I’m the kind of person who starts getting kinda nervous / When I’m having the time of my life.” Consistency is Kacey Musgraves’ best attribute throughout the course of her third studio album, Golden Hour. The song at hand, “Happy & Sad” isn’t among the gems necessarily, but, like everything else, it’s consistent and enjoyable.

Also, worth noting is the fact that it’s both groovy and mellow, while regarding the lyrics and form, the chorus is the centerpiece. As the title suggests, Kacey Musgraves is feeling happy and sad simultaneously – bittersweet?

“Is there a word for the way that I’m feeling tonight?
Happy and sad at the same time
You got me smiling with tears in my eyes
I never felt so high
No, I’ve never been this far off of the ground
And they say everything that goes up must come down
But I don’t wanna come down.”

“Happy & Sad” previously appeared on the playlist, 11 Totally Happy Songs.

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8. XXXTENTACION, “SAD!”

? • Bad Vibes Forever / EMPIRE • 2018

“SAD!” keeps things ‘short and sweet’ on ?, the sophomore album by the late XXXTENTACION. The production is moody and mysterious initially, gradually adding more details. The smoothness and vibe of the musical backdrop is a major selling point, despite the fact that XXXTENTACION shares his feelings of brokenhearted-ness.

Following a 25 second intro, he unveils the chorus:

“Who am I? Someone that’s afraid to let go, uh
You decide if you’re ever gonna let me know (yeah)
Suicide if you ever try to let go, uh
I’m sad, I know, yeah, I’m sad, I know, yeah.”

Apparently, XXX’s depression (his sadness) is incredibly pronounced, considering he’s willing to commit “Suicide if [she] ever tries to let go.” Beyond the central chorus, there’s only one verse, which continues to focus on his broken heart.

“I gave her everything
She took my heart and left me lonely
I’ve been broken, heart’s contentious
I won’t fix, I’d rather weep…”

“SAD!” previously appeared on playlists 14 Songs Where Musicians Are ‘In Their Feelings’ and 15 Songs That Center Around Sadness and Depression.

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9. Post Malone, “Rich & Sad”

Beerbongs & Bentleys • Republic • 2018

“Buy me, love, try to buy me, love / Now I’m alone, ‘Ice Box’, Omarion.” Beerbongs & Bentleys, the 2018, Grammy-nominated sophomore album by breakout pop-rapper Post Malone was dominated by two big-time hits: “Rockstar” and “Psycho”. The extremely commercially successful Beerbongs and Bentleys also marked a critical improvement from his sketchy debut album, Stoney. Post Malone gets ‘in his feelings’ on the sleekly produced, moody “Rich & Sad.” 

 

Despite the sadness, “Rich & Sad” is in a major key, and there’s still a brightness about it – weird.  The melodic chorus is the biggest selling point, where Malone wishes “the money made you stay.” As The Beatles once sung, “Can’t Buy Me Love”:

“Ayy, I would throw it all away
I just keep on wishin’ that the money made you stay
You ain’t never cared about that bullshit anyway
I just keep on wishin’ that the money made you stay.”

“Rich & Sad” previously appeared on the playlists  9 Songs That Thrive Off Being ‘Rich’ and 15 Songs That Center Around Sadness and Depression.

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10. Khalid, “Another Sad Love Song”

American Teen • RCA • 2017

In 2017, teen R&B singer Khalid quickly became one of the hottest names in R&B. Ahead of his highly anticipated debut album, American Teen, he released seven singles, including the crown jewel, “Location”. “Location” gave the Khalid a true breakthrough, setting him up for a potentially successful career. Beyond “Location,” American Teen is filled with a number of terrific moments, including the song at hand, “Another Sad Love Song.”

Khalid doesn’t miss a beat with the groovy “Another Sad Love Song,” the fourth track off of his debut LP. The record easily gets stuck in the head, particularly the chorus:

“Bridges they are burning
Lover, I am worried
Tables are turning
Lover, I am hurting
Burning, burning, burning, dadada…
Turning, turning, turning, turning, dadada…
Burning, burning, burning, dadada…
Turning, turning, turning, turning, dadada…”

As ‘sad’ as the ‘love song’ may be, it’s hard to tell, given the joyful sounds of the production work.  Still, the lyrics suggest heartache on the part of, Khalid, who delivers a compelling vocal performance.

“…I must be honest, I have a lot of pride
But I’m broken inside
I guess this sounds like another sad love song
I can’t get over how it all went wrong…”

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11. The Avett Brothers, “True Sadness”

True Sadness • Republic • 2016

“But I still wake up, shaken by dreams / And I hate to say it, but the way it seems / Is that no one is fine / Take the time, to peel a few layers / And you will find true sadness.” True Sadness just sounds dreary.  No, not the album itself, but rather the title. Nonetheless, The Avett Brothers aren’t nearly as melancholy as the title suggests, delivering a fine effort with their latest LP.  Yeah, there’s some moments where melancholia is exhibited, but what listener would mind shedding some tears for art’s sake? Of course, title track “True Sadness” is one of those moments and fits the ‘sad’ criteria of this particular playlist.

In the context of True Sadness, “True Sadness” returns the LP to a more familiar place following the experimentation of “You Are Mine” and the devilishly superb “Satan Pulls the Strings.” The Avett Brothers sing about various arduous situations throughout the course of the song, whether it’s financial instability on the first verse (“You were a friend to me when my wheels were off the tracks / And though you say there is no need / I intend to pay you back”), addiction, such as alcoholism on the second verse (“Full grown, I’ve been known to lean on a bottle”), or various evils on the third verse (“Just know the kingdom of God is within you / Even though the battle is bound to continue”). Perhaps “True Sadness” doesn’t reinvent the wheel but it finds The Avett Brothers flexing… at their alternative-folk craft that is.

“True Sadness” previously appeared on the playlist, 11 Honest, True, or Truthful Songs.

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11 SONGS WHERE THE SADNESS IS LEGIT [Photo Credits: AWAL, Bad Vibes Forever, Brent Faulkner, Columbia, EMPIRE, Jonas Brothers, Lauv, MCA Nashville, The Musical Hype, Myylo, Nick Miller, Pexels, Pixabay, RCA, Republic, UMG Records, Inc.]

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