13 Totally Locked Up, Prison Songs | Playlist 🎧

1. Miley Cyrus, “Prisoner”

Ft. Dua Lipa

💿 Plastic Hearts • 🏷 RCA • 🗓 2020

“Prisoner, prisoner, locked up / Can’t get you off my mind, off my mind.” 🎙 Miley Cyrus collaborated with 🏆 Grammy-winning pop artist 🎙 Dua Lipa on 🎵 “Prisoner”, a standout from her 2020 studio album, 💿 Plastic Hearts. On “Prisoner,” Cyrus is turned up, assertive, and definitely brings grit to table.  Likewise, Dua Lipa has a dynamic, cutting voice, with the similar ability to deliver rousing performances with incredible nuance.  Lipa takes the lead on the first verse while Cyrus reclaims the reins on the pre-chorus, splitting the energetic, memorable chorus with Dua. Then, roles flip flop with Cyrus taking the second verse, Lipa singing most of the pre-chorus, and Cyrus leading much of that unforgettable chorus.

“Prisoner, prisoner, locked up
Can’t get you off my mind, off my mind
Lord knows I tried a million times, million times, oh-woah
Why can’t you, why can’t you just let me go?”

Besides strong, passionate vocals (“I tasted Heaven, now I can’t live without it / I can’t forget you and your love is the loudest”), Cyrus and Lipa get sweet production work courtesy of 🎛 The Monsters & Strangerz and 🎛 watt.  Ultimately, Cyrus and Lipa ‘do the damn thing.’  Add passionate lyrics, a minor key, and excellent production and “Prisoner” is a certified bop.

Also appears on 🔽:

🔗 🎧 Awesome Songs That Tickled My Fancy: November 2020

🔗 🎧 Prison: 5ive Songs No. 68 (2021)

2. Raphael Saadiq, “Rikers Island”

💿 Jimmy Lee • 🏷 Columbia • 🗓 2019

Eight years.  That’s how long it had been since Grammy-winning R&B musician 🎙 Raphael Saadiq released a new studio album.  Saadiq returned in 2019 with a contemporary masterpiece – his very personal, socially-changed, fifth studio album, 💿 Jimmy Lee.  The crown jewel of Jimmy Lee is 🎵 “Rikers Island”, where Saadiq sings, “Too many niggas in Rikers Island / Why must it be?” The powerful, socially-changed chorus, continues, “Too many niggas in Rikers Island / Set ‘em free.”

Saadiq begins an entirely new conversation on “Riker’s Island,” and it’s not merely limited to the infamy of Rikers Island itself. The big takeaway is the statement that Saadiq makes about the number of black men that are incarcerated.  Yes, Rikers Island is a universally panned correctional facility, but the theme transcends beyond it.  It’s amazing that this record with disturbing, hurtful subject matter for black families that is also the funkiest joint of the album.  One upping that, it ranks among the very best songs of 2019.

Also appears on 🔽:

🔗 🎧 11 Awesome Songs That Tickled My Fancy in September 2019

🔗 🎧 17 Songs Characterized by Their Place.

🔗 🎧 51 Best Songs of 2019: Year in Review

3. Elvis Presley, “Jailhouse Rock”

💿 Elvis 30 #1 Hits • 🏷 Sony Music Entertainment • 📅 2002

“Let’s rock, everybody, let’s rock / Everybody in the whole cell block / Was dancing to the Jailhouse Rock.” Woo! There are few prison or jail-related songs that are more infectious than 🎵 “Jailhouse Rock” – FACTS! Rock icon 🎙 Elvis Presley would end up having a slew of hits in his short lifetime of just 42 years.  That said, if only one of those hits had caught on, ‘The King’ would’ve solidified his legacy.  Of course, the energetic, novel, and vintage 1957 gem “Jailhouse Rock” ranks at the top of his catalog.

“Jailhouse Rock” was penned and produced by the heavyweight team of 🎼 ✍ 🎛 Jerry Lieber and 🎼 ✍ 🎛 Mike Stoller. Lyrically, it’s tongue-n-cheek (“You shoulda heard those knocked out jailbirds sing”), but that’s part of the novel charm.  Of course, it makes sense that there’s outlandish, absurd stories given it’s the title track of Presley’s movie, 🎦 Jailhouse Rock.  Also, it was the 1950s, a starkly different time.

“Number forty-seven said to number three
‘You the cutest jailbird I ever did see
I sure would be delighted with your company
Come on and do the ‘Jailhouse Rock’ with me.’”

Still, decades after this groovy juggernaut was born, it remains timeless, led by the charismatic, gifted Elvis.

4. Miranda Lambert, “Way Too Pretty for Prison”

Ft. Maren Morris

💿 Wildcard • 🏷 Vanner / Sony • 📅 2019

“But we’re way too pretty for prison / Hard time ain’t our kind of livin’.” 🎵 “Way Too Pretty for Prison” is a fun, novel, tongue-n-cheek cut from the 2019 Grammy-winning, 🎙 Miranda Lambert country album, 💿 Wildcard.  There’s another key component, rather artist, that’s part of “Way Too Pretty for Prison.” That would be Lambert’s fellow Grammy-winning colleague, Maren Morris.  Safe to say, these two make awfully sweet music together and are definitely both too pretty for prison!

“Way Too Pretty for Prison” is a successful record thanks to the pronounced twang and outlandish, southern, countrified lyrics and story line.  Lambert handles the first verse and the first pre-chorus, while Morris makes her first appearance on the chorus alongside Lambert.  Of course, on the second verse, Morris kicks things off with a bang singing about “Antifreeze and Gatorade / Arsenic in his lemonade…” Whoa! Morris sings the second pre-chorus before the remainder of the song, including the bridge, finds the two jailbirds, I mean, naughty ladies, singing jointly.

“...And I don’t want to talk about
The way those jumpsuits wash us out
We're way too pretty for prison.”

5. Akon, “Locked Up”

💿 Trouble • 🏷 2004 • 📅 UMG Recordings Inc.

“My car is stolen / No registration / Cops patrollin’ / Now they done stoop me and I get locked up.” In 2004, Senegalese American rapper/singer 🎙 Akon had his breakout moment.  That moment arrived thanks to 🎵 “Locked Up,” the opener and a highlight from his 2004 debut album, 💿 Trouble.  Unless we’re referring to sports and ‘locking up’ a particular seed or playoff berth, typically the phrase ‘locked up’ is associated with incarceration.  That is the case on this minor-key gem that’s produced and written by Akon. Worth noting, a remix features rapper 🎙 Styles P.

As the aforementioned lyrics made clear, Akon was doing stuff he had no business doing, hence he goes in the slammer.  The chorus, the crown jewel of “Locked Up” confirms his incarceration, hence, “They won’t let me out.” The second verse, with Akon singing in his distinct tone, finds him hustling.  Of course, “As I sold the last bag / Fucked around and got locked up.” He had it coming? Cue up 🎵 “Cell Block Tango” or maybe, 🎵 “Cell Block Django” if you want a little parody!  In all seriousness though, “Locked Up” definitely marked one of the most successful parts of Akon’s career.

6. Alec Benjamin, “Mind is a Prison”

💿 These Two Windows • 🏷 Alec Benjamin • 📅 2020

“Guess my mind is a prison and I’m never gonna get out.” 🎵 “Mind is a Prison” commences 💿 These Two Windows in compelling fashion. Blessed with a distinct tone, 🎙 Alec Benjamin delivers gorgeous vocals, singing with both ease and expression. “Sometimes, I think too much, yeah, I get so caught up / I’m always stuck in my head.”  Ah, as awesome as his vocal performance is, the theme is where his ‘bread is buttered’ on “Mind is a Prison.” As the title suggests, Alec captures the power of the mind, in all its dangerousness.  Basically, he paints a picture lyrically about how it’s difficult to escape his own thoughts, much like prison.

Alec nails it on the chorus, setting up mental imprisonment perfectly. He also does swell on the verses setting up mental anguish. He cleverly sings, on the first verse, “I don’t live in California, I’ll inform you, that’s not where I reside / I’m just a tenant, paying rent inside this body and I.” On the second verse, he specifically addresses his state of mind, singing, “I’m a prisoner, a visitor inside my brain.”

Also appears on 🔽:

🔗 🎧 Prison: 5ive Songs No. 68 (2021)

7. The Weeknd, “Prisoner”

Ft. Lana Del Rey

💿 Beauty Behind the Madness • 🏷 Republic • 📅 2015

“When I say that I would be nothing without your love / I feel the rush and it’s amazing.” Well, that’s positive at least, assuming we’re not literally talking about drugs! 🎵 “Prisoner” appears as the penultimate record on 💿 Beauty Behind the Madness, the breakout album by Grammy-winning Canadian R&B artist, 🎙 The Weeknd (Abel Tesfaye).  Beauty Behind the Madness was an album chocked-full of hits including 🎵 “The Hills”, 🎵 “Can’t Feel My Face”, 🎵 “Earned It (Fifty Shades of Grey)”, and 🎵 “In the Night”.  That said, it’s hard not to mention a duet between two dynamic singers like Tesfaye and featured guest, 🎙 Lana Del Rey.

“Prisoner” is another ‘sweet’ moment from Beauty Behind the Madness, even if it ends up being overshadowed by the aforementioned hits.  The Weeknd and Lana Del Rey end up having great chemistry, hence why it’s unsurprising they’ve collaborated since (“Lust for Life” in 2017).  On this sleeky produced (The Weeknd and 🎛 Illangelo), moody number, both are/have been imprisoned to unhealthy things.  This is best showcased on the chorus, which they sing together:

“I’m a prisoner to my addiction
I’m addicted to a life that’s so empty and so cold
I’m a prisoner to my decisions
Woooo, woooo, woooo.”

The outro, by Del Rey, is particularly intriguing as she asserts, “I get so wrapped up in a world where nothing’s as it seems / And real life is stranger than my dreams.” That’s quite telling for sure.

8. Bastille, “Four Walls (The Ballad of Perry Smith)”

💿 Wild World • 🏷 Virgin • 🗓 2016

“These four walls to keep you… / These four walls to contain you / Supposed to save you from yourself…” The somber 🎵 “Four Walls (The Ballad of Perry Smith)” is among the most beautiful, thought-provoking moments of 💿 Wild World, the intriguing sophomore album by British alternative collective, 🎙 Bastille, fronted by 🎙 Dan Smith.  As beautiful as “Four Walls (The Ballad of Perry Smith)” is, the subject matter isn’t beautiful.

“And now we’re faced with two wrongs… / I don’t know, oh, I don’t know.” Perry Smith was a mass murderer who was executed by hanging.  Dan denounces the mass murder’s actions but argues against execution and capital punishment as atonement.

“We could be born to anything and now what, now what?
What you have done is terrible, and now you, and now you
Now you carry it with you
You carry it with you
You carry it with you.”

Also appears on 🔽:

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🔗 🎧 12 Intriguing Songs That Reference Walls 

9. Matt Berninger, “Serpentine Prison”

💿 Serpentine Prison • 🏷 Concord • 📅 2020

“Total submission, I’ve seen a vision / Everyone’s screaming, I’ve been daydreaming / Sorry I’m fishing without permission / Tell her I’m missing in a serpentine prison.” In 2020, 🎙 Matt Berninger, best known as the front man of the 🏆 Grammy-winning alternative collective 🎙 The National, released a solo album, 💿 Serpentine Prison.  The ten-track album concludes with the moderately-paced ballad, 🎵 “Serpentine Prison.” 

Here, Berninger totally compels with his cool baritone vocals.  He never gets too high during his performance, keeping things casual, delivering the poetic lyrics with ease.  Speaking about the song’s conception, Berninger asserts, via the YouTube video description, “The title is from a twisting sewer pipe that drains into the ocean near LAX. There’s a cage on the pipe to keep people from climbing out to sea.”

Also appears on 🔽:

🔗 🎧 Prison: 5ive Songs No. 68 (2021)

10. TOOL, “Prison Sex”

💿 Undertow • 🏷 Tool Dissectional / Volcano Entertainment II • 📅 1993

“I have found some kind of temporary sanity in this / Shit, blood, and cum on my hands / I’ve come ‘round full circle.” Yikes, yikes, and again I say YIKES! First things first, though. When a song is named 🎵 “Prison Sex,” there’s honestly no way that it can’t be controversial, right? RIGHT! I mean, honestly, “Prison Sex” simply isn’t the first title that comes to mind when writing a song. Anyways, “Prison Sex” appears on the 1993 🎙 TOOL album, 💿 Undertow.

“My lamb and martyr, you look so precious
Won’t you, won’t you come on a bit closer
Close enough so I can smell you
I need you to feel this
I can’t stand to burn too long
Release in sodomy
For one sweet moment I am whole.”

What the actual ‘fizzuck?’ If you couldn’t tell, “Prison Sex” tackles the sickening, troubling subject matter of sexual abuse, specifically child sexual abuse. YUCK! Besides the disturbing tone of the song, the music video, which uses stop motion, might be more disturbing than the song itself.  Of course, there was censorship in given cases even using stop motion to depict a, um, unsettling situation and cycle.  That cycle of events is perfectly captured in the aforementioned lyrics, as well as the chilling closing lyrics, “My lamb and martyr, this will be over soon / You look so precious, you look so precious.” 🎙 Maynard James Keenan – always one of a kind.

11. Devin Dawson, “Prison”

💿 Dark Horse • 🏷 Warner Music Nashville • 📅 2018 

“Call me a convict, I’ve been convicted / Serving the verdict, a live sentence.” Wow – that’s not good 🎙 Devin Dawson.  Worth noting, the California country musician released his debut album, 💿 Dark Horse, in 2018.  One of the standouts is 🎵 “Prison,” which appears as the penultimate track.  Basically, the tables have been turned on a guy who’s “Stole some hearts but dodged the bars out on the run.”

That’s right! This lady has totally imprisoned him and his days of committing crimes are done.  You’ve got to love the dramatic nature of the production during the imprisoned chorus, where Dawson rises to the occasion and the country gets a dash of rock.  “You’ve got me locked up / Go on and throw away the key,” he sings, later adding, “I ain’t ever gonna break this prison / … Your love is like a prison.”

Also appears on 🔽:

🔗 🎧 Prison: 5ive Songs No. 68 (2021)

12. Ryan Adams, “Prisoner”

💿 Prisoner • 🏷 PaxAmericana / Blue Note • 📅 2017

From the start of 🎵 “Prisoner,” the title track of 🎙 Ryan Adams’ 💿 2017 album, the lyrics and theme are accessible – highly relatable.  Adams sings on the first verse: “Free my heart / Somebody locked it up / Still waiting on parole / I can taste the freedom just outside that door…” Essentially, on this straightforward pop/rock record, he touches on the power of love – sheer infatuation.

Adams sums up these feelings on the simple, yet memorable refrain:

“I know our love is wrong
I am a criminal
Mmm, I am a prisoner
Mmm, I am a prisoner
For your love.”

Well produced, “Prisoner” embodies the spirt of rock and singer/songwriter.  The dash of harmonica is like the cherry on top.

Also appears on 🔽:

🔗 🎧 Prison: 5ive Songs No. 68 (2021)

13. Johnny Cash, “Folsom Prison Blues”

💿 At Folsom Prison • 🏷 Sony Entertainment • 📅 1968

“I’m stuck in Folsom prison, and time keeps draggin’ on / but that train keeps a rollin’ on down to San Antone.” One of the most iconic musicians of all time was none other than the late, great 🎙 Johnny Cash.  One of his greatest songs of all time was 🎵 “Folsom Prison Blues,” which we could never omit from any prison or jail-centric playlist.  The key recording of “Folsom Prison Blues” appears on an iconic live album, 💿 At Folsom Prison, released in 1968.  This particular record masterfully encompasses country, specifically outlaw country, rock, and references the blues.

“Folsom Prison Blues” fittingly commences the live album, capturing a narrative of how the protagonist ends up in prison.  Was Johnny Cash really incarcerated in Folsom Prison? No, but his imaginative narrative is incredible – #ICONIC! The second verse might be my favorite:

“When I was just a baby, my mama told me, ‘Son
Always be a good boy, don’t ever play with guns’
But I shot a man in Reno, just to watch him die
When I heard that whistle blowing, I hang my head and cry.”

Of course, he couldn’t get away with murder… well, it happens, but it shouldn’t.  On that note, we conclude this compendium!