13 Deep Songs Where the Depth is Real | Playlist 🎧

1. Adele, “Rolling in the Deep”

25 • XL Recordings • 2011

Nine words: “We could have had it all / Rolling in the Deep.” Adele had already garnered buzz with her debut album, 19, which earned her first two Grammy wins.  That said, “Rolling in the Deep” from 21 definitely had a much bigger impact than “Chasing Pavements” could’ve ever hoped for (and “Chasing Pavements” was quite underrated BTW).  “Rolling in the Deep” was a ubiquitous number one hit – a crossover masterpiece.

Where style is concerned, “Rolling in the Deep” fuses pop, soul, gospel, and retro superbly. Adele herself describes it as “gospel disco.” The minute I heard it, I knew she had a surefire winner on her hands.  In addition to powerhouse vocals and awesome production, the theme and songwriting are top-notch.  Basically, her man wronged her, she’s done with him, and there’s definitely going to be hell pay – “You’re gonna wish you – never had met me.”  No surprise that “Rolling in the Deep” won four Grammys by itself (including Record and Song of the Year), in addition to 21 winning two, most notably Album of the Year.

2. Eminem, “In Too Deep”

Music to Be Murdered By • Shady/Aftermath/Interscope • 2020

“In Too Deep” appears on Music to Be Murdered By, the 2020 surprise studio album by iconic rapper, Eminem.  Eminem has remained prolific when it comes to releasing new music, BUT his music hasn’t been quite as, um, ‘elite’ as it once was.  Regardless, Music to Be Murdered By is an improvement for the rapper.

Is “In Too Deep” the crème de la crème of Music to Be Murdered By? No, but it’s worth a listen or to.  The record features straight, un-pitched rhymes on the verses, and more modern, melodic vocals on the chorus. No problem there, all in all. The overall effect is a hip-hop record with some R&B cues that explores a bad relationship where both parties are clearly ‘in too deep’.

“I’m not happy here (Nah), with her
Rather have you (Yeah), rather have me too
‘Cause you’re not happy there (You’re not happy there), with him
Rather have me (I know, but), we just in too deep.”

3. Fousheé, “Deep End”

“Deep End” • 2020

Fousheé seems destined to do big things, period. The R&B singer is on [autopilot] from the start of “Deep End”. This brief record – a mere two minutes and 21 seconds – is incredibly potent.  Backed by a vibe-filled backdrop, “Deep End” is fresh, moody, and set in a minor key. Primarily R&B, there are hip-hop sensibilities, which only make things fresher.  It commences with an intro, which eventually becomes the chorus (the crowning achievement).

“I been trying not to go off the deep end
I don’t think you wanna give me a reason...”

Fousheé gives us commanding, expressive, and nuanced vocals.  Furthermore, she conveys a big personality, which speak to her artistry.  She’s classy but also unafraid to bring in some ‘stank.’ Sung vocals dominate, however, she’s equally effective when she ‘busts a rhyme.’ Also, totally worth checking out is the brief but potent “Deep End Freestyle”, attributed to Sleepy Hallow and Fousheé.

4. Bee Gees, “How Deep is Your Love”

Timeless – The All-Time Greatest Hits • Capitol • 2017

“How deep is your love / How deep is your love / I really mean to learn …” “How Deep is Your Love” is an iconic song – a classic.  Bee Gees were an iconic pop collective, with the height of their fame occurring during the 1970s – disco was indeed king! “How Deep is Your Love” famously appeared on the Saturday Night Fever soundtrack, still among the best soundtracks of all time – I dare you to dispute it!

So, what makes “How Deep is Your Love” one of the best deep songs (or otherwise) ever performed and written? Stellar vocals and harmonies, first and foremost. Sadly, there will never be another Bee Gees, sigh. The song itself checks off all the boxes: memorable lyrics, relatable theme, gorgeous, tuneful melody, and ear-catching, lush production work.  The song has been covered effectively by numerous artists including PJ Morton.  That said, none eclipses the original.  As for the rest of the chorus, well, it goes a little something like this:

“‘Cause we’re living in a world of fools
Breakin’ us down
When they all should let us be
We belong to you and me.”

5. Lecrae, “Deep End”

Restoration • Reach • 2020

“I’ve been tryin’ not to go off the deep end / Give me a reason / I’ve been tryin’ not to.” John Summit – we definitely don’t want you to do that! Summit, by the way, is sampled on “Deep End,” the sixth track on Restoration, the 2020 studio album by rapper Lecrae.  The sample has been slowed down compared to the original, with additional dramatic production by MrWriteNow.

Lecrae delivers an awesome flow – something we’ve come to expect from the rapper over the years.  He sounds agile, expressive (vocal inflections, breaths, etc.), and incredibly energetic. On “Deep End,” he’s open and honest about wrestling with faith, and about his feelings regarding the issues plaguing the world (racial inequality, police brutality, coronavirus).  Of course, the big takeaway is that God prevented him from going ‘off the deep end’ and has helped  him and continues to help work through all of this.  Sure, “Deep End” is spiritual like most Lecrae songs, but also, he keeps things fresh and interesting, particularly with the woke pop cultural references (“Yeah, I might go crazy / I might go MJ back in the 80s”).

6. Cupcakke, “Deepthroat”

Cum Cake • cupcakKe • 2016

“Hump me, fuck me / Daddy better make me choke / Hump me, fuck me / My tunnel loves to deep throat / Lick, lick, lick, lick (I lick it) / I want to eat yo dick (I do).” What the… You know what’s hard to believe? CupcakKe started out as a church poet.  On the totally X-rated “Deepthroat,” she amplifies sex to the nth degree – understatement! “Deepthroat” hails from the rapper’s inappropriately titled 2015 album, Cum Cake.  Yeah, that totally sounds delicious… The ‘subtlety’ of the hook (aforementioned) is also a sight to behold… said no one ever.

“Mouth wide open, mouth wide open
Mouth wide open like I was at the dentist
Mouth wide open, mouth wide open
Put it so deep, I can’t make a sentence.”

The big takeaway from “Deepthroat” is that it’s a record that’s totally TMI. CupcakKe truly pushes the envelope, adding even more absurd, over-sexed rhymes that publicize the bedroom where it would be better served private.

“My fingers in it, gentle
Explore this n***a mental...
My pussy pink just like salami...
My pussy mean, and it’s clean
I’m not a squirter, I cream
Keep it smelling like baby wipes
I never smell like sardines...
This will never fucking end
Ballerina that dick when I spin
I fucked this n***a so good
I ain’t swallow one kid, I think I swallowed twins.”

“Deep Throat” in all its absurd, explicitness, has appeared on multiple lists including 10 Filthy Songs by Female Rappers, 11 Songs That are X-Rated, to Some Extent, and more recently, 15 Songs Where Female Rappers Gettin’ Down ‘N’ Dirty.

7. Tame Impala, “Breath Deeper”

The Slow Rush • Island • 2020

The groovy “Breathe Deeper” marks another cut on The Slow Rush that extends beyond six minutes in duration.  Whoa Nelly – hold TF up! Backtracking a bit, and providing some context, The Slow Rush marked the first new Tame Impala album in nearly five years (Currents, 2015). The record may run long, but it’s quite a glorious listen. It can’t be overstated how great Tame Impala is with neo-psychedelia – it’s definitely Kevin Parker’s thing.

Yes, neo-psych is easily perceptible, but “Breathe Deeper” also manages to be quite soulful, with the ostinato keyboard passages and synths hearkening back to 70s funk, soul, and disco. Furthermore, it’s poppy too! The lyrics are simple, but potent, yielding a top-notch chorus, not to mention catchy verses too (“If you think I couldn’t hold my own, believe me, I can”).

8. Summer Walker, “Deeper”

Life on Earth (EP) • Interscope • 2020

“Boy, you say you’re done with games and more / We gotta get deeper now.” That’s right – kick things up a notch and take it to the next level! Post-Over It, Summer Walker dropped a five-song, 16-minute EP in Life on Earth in 2020. Life on Earth embraces the ‘vibe-laden culture’ of today’s R&B.  It’s a bit liter than some R&B preceding it. Walker concludes her 2020 EP, Life on Earth, with “Deeper.”

Sexy guitar accompanies equally sexy, smooth vocals by Walker. If you’ve followed her up to this point, you can pretty much predict the script.  Walker is more of a cooler presence than a dynamic one, something that holds true on “Deeper.”  “Deeper” is a successful, well-rounded record overall, though certainly not groundbreaking or game changing.  What I’m saying is – it’s not that deep!

9. Daniel Caesar, “TOO DEEP TO TURN BACK”

CASE STUDY 01 • Golden Child Recordings • 2019

“So, what’s the price / We’re like mosquitos to light, in a sense / I feed off bioluminescence…” Case Study 01 is complex, yet rewarding project by Grammy-winning, Canadian R&B singer/songwriter Daniel Caesar. Unfortunately for Caesar, some controversy hurt the performance of this album – yeah, he was cancelled, at least to some extent.  Regardless, the lovely “Too Deep to Turn Back” provides evidence of the rewarding nature of the album.   

Daniel Caesar sounds fantastic, never needing to ‘break a sweat’ to pack a punch on “Too Deep to Turn Back.”  Here, religion plays a significant role, specifically on the chorus, which features vocals by Arianna Reid, as well as the fourth verse:

“I’ve slept like Jacob, a rock for a pillow
Run swift like Elijah, away from the middle.”

Caesar is often at his best when he weaves spirituality in a secular genre like R&B.

10. Drake, “Deep Pockets”

Dark Lane Demo Tapes • OVO / Republic • 2020

Drake and vibe are synonymous, and I double dare you to dispute that.  Anyways, the ‘6 God’ commences his demos album (or mixtape would be more accurate), Dark Lane Demo Tapes with the vibe-laden “Deep Pockets.” “Deep Pockets” features production by Noah “40” Shebib and Plain Pat.  The sound is cloudy, laid back, and lush.  While the backdrop lacks finesse where a clear, crisp sound is concerned, it suits Drake perfectly.  His flow provides an excellent contrast.

“Yeah, then we rollin’, then we rollin’
Deep pockets on a n***a, I can’t find my phone in
Now we rollin’
Yeah, then we rollin’, then we rollin’
Deep pockets on a n***a, I can’t find my phone in
Now we rollin’.”

11. Kehlani, “Too Deep”

While We Wait • Interscope • 2019

Kehlani is an incredibly talented singer.  Not everybody can release mixtapes that have their fair share of bops just like studio albums. While We Wait, released in 2019, was a great ‘in-between’ project with its fair share of respectable songs. Heck, “Nights Like This” was a hit – among the crème de la crème of 2019.  While “Too Deep” wasn’t a commercial hit, it marked a solid, enjoyable moment from the tape.

“Too Deep” finds Kehlani being blunt – she’s at her best when she keeps it 💯.  She asserts on the first verse, “I thought we were just fuckin’ / I can’t fall in love for nothin’.” There it is! She’s frank on the centerpiece, the chorus – you definitely know where she stands! Love is merely out of the question:

“But this shit getting too deep
Too deep
Too deep for me.”

As always, Kehlani delivers marvelous vocals.  The production work is strong and clearly idiomatic of contemporary R&B

12. Lykke Li, “Deep End”

So sad so sexy • RCA • 2018

Following a four-year hiatus, alternative singer/songwriter Lykke Li returned in 2018 with her fourth studio album, so sad so sexy. The crème de la crème comes by way of “deep end.” Produced by T-Minus, Malay, and Jeff Bhasker, it’s not surprising how hip, slick, and thoroughly modern the record sounds.

Beyond the killer, minor-key, the Swedish singer successfully performs this well-written number. The best moment comes by way of a feisty, infectious,

‘swim-referencing’ chorus.

“Swimming pool, swimming pool
Swimming pool, swimming pool
Indigo, deep blue, deep blue
Oh, baby I know where you’ve been
I know where you been, in the deep end.”

This isn’t really about the pool but rather, L-O-V-E. “Deep end” most recently appeared on Swimming…5ive Songs No. 22 and 11 Summery Songs Loosely Associated with The Beach.

13. Jon Bellion, “Stupid Deep”

Glory Sound Prep • Capitol • 2018 

In the context of Glory Sound Prep, the sophomore album by Jon Bellion, the arrival of “Stupid Deep” provides contrast – thoughtful balladry. The production is bright and optimistic, characterized by its use of keyboards and synths.  Vocally, Bellion sounds beautiful, nuanced, and incredibly tender in his execution, that is until he grows grittier and more dynamic towards the end.  The chorus is the centerpiece, followed by an instrumental feature.

“What if who I hoped to be was always me?
And the love I fought to feel was always free?
What if all the things I’ve done
Were just attempts at earning love?
But the hole inside my heart is stupid deep, oh, stupid deep.”