Welcome all to another FiveOnFridays here on Introverted-Insight! And once again, it’s time for one of my favorite segments called “Playlist Chronicles”. If you so happen to be unfamiliar with the concept, here’s the gist.
So basically, I delve into my personal music library on my phone, scroll through all the tracks until I come up with a playlist tailored to a specific theme or topic, then I write about it.
I feel it’s great a way to introduce you all to a lot of new music, give you a better idea of my musical palette, and remind me of what’s actually in my library. Therefore, every song on this list, along with the honorable mentions are exclusively from my personal library.
Explanation aside, this week I’ll be looking at 5 songs that pierce my heart and break my soul (what’s left of it) every time I listen to them.
These are the type of songs I keep on repeat because of their ability to emotionally capture me, even though they’re high-key depressing. But the good kind of depressing, you know?
Okay, that’s enough chatter from me; let’s get this countdown started!
#5. Brandi Carlile – Sugartooth
Admittingly, the very first time I heard this song I shed a few tears. I was already deeply engrossed by Brandi’s ‘By The Way I Forgive You’ album and allowed the vividly telling narrative to get the better of me.
The gentle strings coupled with Brandi’s storytelling skills masterfully set the country tone of the song. As backing vocals harmonize sweetly during the track’s chorus and bridge, more flair is added to the mix. Additionally, the energy of the song pendulums consistently between moments of calm and passion.
But what truly makes it devastating are Brandi’s vocal performance and the lyrics. It finds her translating her feelings of sorrow and remorse for this persona, whose ‘Sugartooth’ (a euphemism used for drug addiction) eventually led to his demise. The songwriting here is brilliant. Lines such as “And I heard they put what was left in a box/ And took it to a place called Jesus Rock”, make you frown upon the misfortunes of life.
All in all, the unwholesome story of this man’s life would convince listeners that he truly was “Living proof that there was no God/ Just the devil stiff as a rod”. For what started out as a calm timeline of someone’s life gradually turned into an emotional torrent of despair, which couldn’t be more precious.
#4. Azealia Banks – Soda
Do not be fooled by the upbeat composition of the song; as you pry deeper into its lyrics, you start to feel how insidiously sad it truly is. A noisy haze slowly envelopes you in the beginning of the track before you meet the acquaintance of some peppy drums. Banks then enters with steady vocals and very unsettling lyrics following the chorus.
“A smile a guise/ I’m trying to hide behind tired eyes, I sigh/ I might survive the nighttime, I might die”. With words now properly registering, you realize that she’s desperately trying to mask the pain she’s feeling. Throughout the song, she uses ‘Soda’ (commonly used in various alcoholic drinks) to reference her ongoing substance abuse.
Hence, “I say soda, soda!”. She’s saying yes to the distraction, despite being completely aware of the health risks involved. As the song progresses, the electronic flavors place you in a sea of gloom and heavy reflection. Soon you learn that Banks is devastated by a break-up and has lost her sense of self when she lost her lover.
Toiled in confusion, she becomes increasingly self-aware of her tumultuous state, repeatedly singing “I used to be your girl, girl”. Ultimately, the uncertainty lining the lyrics sharply contrast the pulsing production. Yet, they both manage to meet each other halfway to create a cerebral experience that jostles with your emotions.
#3. SZA – Drew Barrymore
First of all, SZA’s “Ctrl” album was paid in dust! In my opinion, it didn’t get the accolades it truly deserved, especially from the Grammy’s. And this somber, soulfully sung tune is one of the best highlights from said amazing body of work.
‘Drew Barrymore’ follows the emotional turmoil associated with feeling inadequate in a relationship. It tangos with themes of self-doubt, insecurity, and this constant pressure men (sometimes unknowingly) place on women they’re in a relationship with – this pressure to be the “perfect companion”. Consequently, it all tends to leave the female in an abyss of hurt with rejective thoughts that make her question her own self-worth.
SZA beautifully manipulates her voice throughout the track as the smoky horns and soothing violins ensnare you with their very wining, looming appeal. A prime example of her impressive vocal delivery would be on the song’s hook. She growls at her lover, “Tell me that it’s warm enough here for ya/ Warm enough outside, inside me, me, me, me”.
This song is plea, a cry for any indication that you are enough to satisfy your lover -whether sexually or otherwise. It highlights those dark, private moments we occasionally let consume us while evaluating our relationship. Honestly, you don’t have to be a female to relate to this incredibly, morose masterpiece.
#2. Lorde – Liability
I definitely had difficulty choosing just one song from ‘Melodrama’ for this list. Honestly, that entire album is devastatingly beautiful. However, I think avid Lorde listeners can agree that ‘Liability’ was THE ballad of the record. Its simple piano and Lorde’s raw, moving vocals team-up, encroaching into extremely vulnerability territory.
The song opens you up to a side of yourself you were convinced didn’t truly exist, but it does. Amidst heartbreak, Lorde uses her superb lyricism to convey doleful imagery. “I do my best to meet her demands, play at romance/ We slow dance in the living room, but all that a stranger would see/ Is one girl swaying alone, stroking her cheek”.
Soon enough, you realize that the song is not only about taking responsibility for being the reason a relationship went south. It’s also about getting into the habit of being enough for yourself, finding comfort in your lonesome when others opt to reject you.
This song especially hit home for me when I heard some of the most tear-jerking lines ever. “The truth is I am a toy that people enjoy/ ‘Til all of the tricks don’t work anymore/ And then they are bored of me”. I felt that on a spiritual level and it brought back so many haunting memories and brought forward so many hurtful revelations. Overall ‘Liability’ will leave you distraught, but with a greater appreciation for self.
**Honorable Mentions**
- Lady Gaga – Joanne (Where Do You Think You’re Going?)
- Adele – Hello
- Kesha – Praying
- Dua Lipa – Be The One
- Ed Sheeran – Castle On The Hill
#1. Flume – Never Be Like You ft. Kai
A very frosty chime kicks this song off, bringing you to an immediate sense of enchantment. As Kai’s gorgeous vocals amplify the track’s pulchritude, the subtle keys and light strings create an ethereal atmosphere. Then enters the punchy, trance-inducing production on the chorus!
“I’m only human, can’t you see? I made, I made a mistake/ Please just look me in my face, tell me everything’s okay/ ‘Cause I got it, ooh, he’ll never be like you”, Kai begs as she regrets hurting someone she deeply cares about for someone who was but a fling.
Earlier in the track she made mention of her self-sabotaging tendencies which led to her current state. “What I would do to take away this fear of being loved/Allegiance to the pain”. She’s talking about questioning an opportunity at true happiness because you’re so conditioned to experiencing hurt. Moreover, you choose to be hurt because it’s easier to process due to familiarity – something I find myself deeply identifying with.
This song speaks to what can happen when you question the good in life too frequently. It’s other-worldly production helps heighten the remorse and agony one can endure as a result. It’s one of those songs that’ll take you on an emotional rollercoaster every time. It has a soul all its own that embraces you, especially with headphones on.
Did you enjoy the list? Which song made you weep the most? Let me know in the comment section below.
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Thank you so much for reading and I’ll see you next time on Introverted-Insight!

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Terran Brice
Sidebar: I dare you to not cry after listening to these 5 songs in a row.