Seeking songs with complex lyrics
December 31, 2018 11:12 PM   Subscribe

I get a special enjoyment out of songs with gratuitously clever lyrics. Lots of words with 3 or better yet 4 + syllables. Internal rhyming. Enjambment. Alliteration. Extended metaphors or particularly interesting analogies. Wordplay.

An example: No matter how many times I listen to it I get a little frisson from the line "I'm watching the tenements/increase by increments" in the song Local Construction. I just find the alliteration so satisfying. That song has several other lines that fit what I'm looking for, like referring to the sky as "one big blue taurpalin draped over scenery" (metaphor) or having "the birds interrupt the CAT while it's backing up" (play on words, and possible a deliberate callback to crane earlier but I might be reading too much into it).

Super obvious additional example: Pretty much all of the Hamilton soundtrack.

Help me find more songs like this!
posted by Cozybee to Media & Arts (83 answers total) 43 users marked this as a favorite
Elvis Costello is a great example of what you're looking for.
posted by Calvin and the Duplicators at 11:18 PM on December 31, 2018 [10 favorites]

I would think much of Noël Coward and Cole Porter's oeuvres would suit, if they're not too dated for you. Are you wanting something contemporary?
posted by mumkin at 11:26 PM on December 31, 2018 [2 favorites]

You will enjoy the work of the rapper Shad
posted by bleep at 11:45 PM on December 31, 2018 [4 favorites]

One Week by Bare Naked Ladies?

La Vie Boheme from Rent? (NSFW)
posted by Weeping_angel at 12:05 AM on January 1, 2019

You might like picking up some of what Eric B. and Rakim laid down, like "Follow the Leader."
posted by praemunire at 12:18 AM on January 1, 2019 [1 favorite]

A Weekend in the Country from A Little Night Music and tons of other Sondheim. “Your Fault” from Into the Woods.
posted by Smearcase at 12:18 AM on January 1, 2019

Reunion - Life is a Rock (But the Radio Rolled Me)
posted by rhizome at 12:20 AM on January 1, 2019

Bob from Weird Al
posted by ch3ch2oh at 12:33 AM on January 1, 2019 [1 favorite]

All of Warren Zevon, particularly Desperados Under the Eves "And if California falls into the ocean, like the mystics and statistics say it will, I predict this motel will be standing until I pay my bill..."
posted by lois1950 at 1:34 AM on January 1, 2019 [2 favorites]

all of 90s rap music
posted by kensington314 at 1:35 AM on January 1, 2019 [3 favorites]

Oh yeah, Elvis Costello. And check out Nick Lowe and Dave Edmonds. And then Rufus Wainwright. Then maybe Vampire Weekend.
posted by nicwolff at 1:42 AM on January 1, 2019

Alphabet Aerobics by Blackalicious.

Man In A Hat by the Klezmatics. (First few lines are in Yiddish, but don't be frightened away -- the rest is in elaborately rhymed English.)
posted by yankeefog at 1:43 AM on January 1, 2019

"And though pink elephants I'd see/though I'd be drunk as I could be/Still I would sing my song to me/About the time they called me Jackie ..."
posted by Rube R. Nekker at 1:53 AM on January 1, 2019 [1 favorite]

Check out XTC, beginning with You and the Clouds Will Still be Beautiful.
posted by she's not there at 1:54 AM on January 1, 2019 [4 favorites]

Most of Tim Minchin's stuff is full of very clever comedy. Start with Thank You God if you're OK with religious satire (one of my favourite lines is about omnipotent ophthalmologist). Follow it up with Prejudice.
posted by cholly at 2:37 AM on January 1, 2019 [5 favorites]

Stephin Merritt (Magnetic Fields + other bands) is a master of this. Think Porter/Gershwin/Tin Pan Alley mixed up with 80s new wave.

Zebra: "we've got so many tchotchkes we've practically emptied the Louvre / in most of our palaces there's hardly room to manoeuvre"
Meaningless: "meaningless / like when two fireflies fluoresce / just like everything I guess / bless us, yes, it was utterly meaningless"
posted by equalpants at 2:39 AM on January 1, 2019 [14 favorites]

Paul Simon (sans Garfunkle) certainly had a way with words.
posted by Weeping_angel at 2:49 AM on January 1, 2019 [5 favorites]

Much of the Sparks' catalogue!
My favourite:
Beat the clock
posted by bluedora at 3:36 AM on January 1, 2019 [1 favorite]

Maybe the Decembrists: Lyrics. Also, some of Dougie MacLean's songs, for metaphors.
posted by Botanizer at 3:49 AM on January 1, 2019 [4 favorites]

Leonard Cohen is excellent in this respect (and others). The album More Best Of might be a good starting point.
posted by sueinnyc at 3:49 AM on January 1, 2019 [5 favorites]

If you speak German, Rammstein do a lot of this.
posted by Vortisaur at 3:59 AM on January 1, 2019

Van Der Graaf Generator, and Peter Hammill solo.
posted by Stoneshop at 4:00 AM on January 1, 2019

I immediately thought of "Autobiography" by Sloan.
posted by saladin at 4:36 AM on January 1, 2019 [3 favorites]

I go to work by Kool Moe Dee has some very clever bits.
posted by conifer at 4:49 AM on January 1, 2019

For vocabulary, Ted Leo is the only punk rocker I know of to pull off using "historicity" and "ossify" in a song without sounding pretentious.

For wordplay and internal rhyming: Mos Def is an absolute master of multi-syllabic rhymes. "born inside the winter wind the day after december tenth, these simpletons are mentioning the synonym for feminine"
posted by entropone at 5:31 AM on January 1, 2019 [5 favorites]

Ian Dury and the Blockheads - Reasons to be Cheerful, Part 3 (lyrics)
posted by rhizome at 5:33 AM on January 1, 2019 [1 favorite]

Seconding the Sloan recommendation, specifically Chris Murphy’s songs (Jay Ferguson’s are a close second).
posted by stefnet at 5:38 AM on January 1, 2019 [2 favorites]

Nthing Elvis Costello: a few lines from his body of work:

Green Shirt: Somewhere in the Quisling clinic there's a short-term typist taking seconds over minutes. She's listening in to the Venus Line, she's picking out names, I hope none of them are mine. (Practically every single word has an alternate meaning)

Oliver's Army: Call Career's Information, have you got yourself an occupation? If you're out of luck, you're out of work....we can send you to Johannesburg....

Also, the Clash, London Calling: This song is about the hardships of living in London, and the refrain is, "I live by the river" so call is a play on "caul" which is a bit of the embryonic sack left over an infant's face that supposedly protected the child from drowning. Adds a whole layer of meaning to the song.
posted by effluvia at 5:44 AM on January 1, 2019

Das Racist has two freely available mixtapes that are full of these literary/poetic wordplay techniques, also incorporating pop-cultural references.
posted by SaltySalticid at 5:52 AM on January 1, 2019 [2 favorites]

Depending on your tolerance for twee-ish indie pop Los Campesinos! might be up your alley.
posted by corvine at 6:12 AM on January 1, 2019

Joy to your world, it's Paul Barman.
posted by herrdoktor at 6:31 AM on January 1, 2019

Everything by the Weakerthans. Examples: Pamphleteer, Plea From A Cat Named Virtute, Letter of Resignation.

Also Dar Williams: When Sal's Burned Down, What Do You Hear In These Sounds.
posted by Catseye at 6:31 AM on January 1, 2019 [9 favorites]

Tom Lehrer.

The opening of We'll All Go Together When We Go:

"When you attend a funeral,
It is sad to think that sooner or
Later those you love will do the same for you.
And you may have thought it tragic,
Not to mention other adjec-
Tives, to think of all the weeping they will do."
posted by Mr.Know-it-some at 6:32 AM on January 1, 2019 [7 favorites]

I think you might get a kick out of some of Andrew Bird's earlier work, starting with Measuring Cups and Heretics.

Armchair Apocrypha full album.
posted by vers at 6:34 AM on January 1, 2019 [3 favorites]

Seconding XTC. "No Language In Our Lungs," is downright poetic. And "Season Cycle" as well.

Aimee Mann would fit the bill as well, I think.

Crash Test Dummies' God Shuffled His Feet is a lyrical treasure trove, though you might not guess it by its most played track "Mmm Mmm Mmm Mmm." Consider instead "When I Go Out With Artists."

The artists of the future
Will make up new things and different nomenclatures
And they'll stand amongst their pictures
And they'll sing and laugh and quote from scriptures and
When they go home they'll dream of brilliant paintings

I've long loved "The Psychic" too.

The Smiths and some of Morrissey's stuff have great lyrics, and I've never failed to smirk at this from "Stop Me If You Think You've Heard This One Before."

I was delayed, I was way-laid
An emergency stop
I smelt the last ten seconds of life
I crashed down on the crossbar
And the pain was enough to make
A shy, bald, Buddhist reflect
And plan a mass murder

posted by jzb at 7:05 AM on January 1, 2019 [1 favorite]

In opera or musical theater, a moderately fast song with complicated lyrics is called a patter song. In particular, the Major-General's Song from Pirates of Penzance might be worth a listen, as might other examples listed on the above-linked Wikipedia page.
posted by Johnny Assay at 7:12 AM on January 1, 2019 [3 favorites]

Elvis Costello, absolutely. ("Spare us the theatrics and the verbal gymnastics/We break wise guys just like matchsticks.") And Paul Simon. (You Can Call Me Al is a particularly good example.)

Maybe try The National. I'm a big fan of Matt Berninger's lyrics. Bloodbuzz Ohio first caught my attention when I heard, "I was carried to Ohio in a swarm of bees." Some other examples:
You can drive a car through my head in five minutes
From one side of it to the other

We'll go from car to sleeping car and whisper in their sleeping ears
We were here, we were here

Oh, come, come be my waitress and serve me tonight
Serve me the sky with a big slice of lemon

You're tall, long legged
and your heart's full of liquor
And me and everybody are just ice in a glass
posted by Redstart at 7:51 AM on January 1, 2019 [2 favorites]

You want Johanna Newsom.
posted by Temeraria at 8:01 AM on January 1, 2019 [6 favorites]

Add to these at least half the music catalog of Phish.
posted by yclipse at 8:27 AM on January 1, 2019 [1 favorite]

Just about everything by Rush.
posted by Enid Lareg at 8:34 AM on January 1, 2019 [1 favorite]

Yes, Joanna Newsom!

"Leaving the City" would be a great intro. It's her most pop-style song to date. On paper it could almost be a hip hop track.

"Emily", written to her sister, an astrophysicist, is more intimate yet grander in scale.

The Beach Boys' "Surf's Up" is miles away from their earlier, simpler, songs about cars, girls, and, well, surfing. Van Dyke Parks (who also did the orchestration for "Emily", incidentally) wrote the lyrics and Mike Love threatened to quit over them
posted by hydrophonic at 8:37 AM on January 1, 2019

The Roches are super into wordplay.

I’ve got the apple in me. Original cinnamon style. - This Feminine Position

I am the only tree, and everybody leaves. -One Season

Sometimes our voices give out, but not our ages and our phone numbers. -We
posted by FencingGal at 9:11 AM on January 1, 2019

Re Weird Al’s Bob, noted above: I’m not sure it’s obvious that every line is a palindrome, which is the real genius of the lyrics.
posted by FencingGal at 9:16 AM on January 1, 2019 [1 favorite]

Anything by John Darnielle, a/k/a The Mountain Goats. Just one of many many examples: Love Love Love.

And a New Year's anthem: This Year. (You have to listen to it to get this, but I *love* the lines "twin high maintenance machines" and "in a calvacade of anger and fear."
posted by merejane at 10:14 AM on January 1, 2019 [6 favorites]

Also -- here's a great article about John Darnielle, whom the author calls "America's best non-hip-hop lyricist."
posted by merejane at 10:18 AM on January 1, 2019 [1 favorite]

Stephen Merritt, primarily his work with The Magnetic Fields, does some fancy wordsmithing.


in Las Vegas where
the electric bills are staggering
the decor hog wild
and the entertainment saccharin
what a golden age,
what a time of right and reason
the consumers king
and unhappiness is treason
posted by jeremias at 10:34 AM on January 1, 2019

Michael Penn! All of MPs albums are great, but Free for All is especially heavy on clever wordplay.
posted by maddieD at 10:34 AM on January 1, 2019

Seconding Andrew Bird, and thinking of his songs “Tenuousness” and “Anonanimal” in particular.
posted by D.Billy at 10:45 AM on January 1, 2019

Agree with several others here re: the Magnetic Fields. The "69 Loves Songs" records are a treasure trove of wordplay.
posted by baseballpajamas at 10:50 AM on January 1, 2019

Yep, Magnetic Fields. The only point of this comment (given that they have already been mentioned three times) is to share another example of their preternatural wordplay:

Let's pretend we're bunny rabbits
Let's do it all day long
Let abbots, Babbitts and Cabots
Say Mother Nature's wrong

I mean, Christ.
posted by aws17576 at 10:56 AM on January 1, 2019 [1 favorite]

Courtney Barnett, especially Avant Gardener for sparkling and gleeful lyrical wordplay.
posted by freya_lamb at 11:19 AM on January 1, 2019 [3 favorites]

They Might Be Giants
posted by exogenous at 12:42 PM on January 1, 2019 [5 favorites]

Uncle Bonsai (three people, more or less; amazing tight harmonies and wordplay) and The Electric Bonsai Band (one guy, pretty much). And The Bobs.
posted by clew at 1:07 PM on January 1, 2019 [1 favorite]

For vocabulary, Ted Leo is the only punk rocker I know of to pull off using "historicity" and "ossify" in a song without sounding pretentious.

Don't forget apostasy. (I love this song.)

Maybe try the Lucksmiths on for size. This one's got "heliolithic."

I've always liked Talib Kweli's verse on this song -- "The ghetto full of betrayal like Iago in Othello, your fellow neighbor will slay you, he'll smoke you like cigarillos, police want that info, they'll grill you like portobellos"

Dessa's verse on The Grand Experiment is a summary of the entirety of human history in sixteen bars. If you like that, there's lots more Doomtree you'll probably like too. There's five different rappers and they're all clever in different ways. (One more. "Hangin' out the van/hailin' cabs in your city" and also "struck by lightning with a hand in the sand/came to with a fist fused in glass".)
posted by clavicle at 1:10 PM on January 1, 2019

I was also going to suggest the Weakerthans for sure. Check out Our Retired Explorer (Dines with Michel Foucault in Paris, 1961), Civil Twilight and My Favourite Chords.
posted by just_ducky at 1:21 PM on January 1, 2019 [1 favorite]

Nearly everything by Sondheim. Into the Woods, A Little Night Music, Sweeney Todd, Assassins. Just one small example:
Did I abuse her
Or show her disdain
Why does she run from me
If I should lose her
How shall I regain
The heart she has won from me
Beyond power of speech
When the one thing you want
Is the only thing out of your reach
If you like Hamilton, there's also In the Heights, also by Lin-Manuel Miranda.

And some David Yazbek:
Where you are, this is not Petah Tikva
Such a city, nobody knows it!
Not a fun, not an art, not a culture
This is Bet Hatikvah, with a "B"
Like in "boring"
Like in "barren"
Like in "bullshit"
Like in "bland"
Like in "basically bleak and beige and blah, blah, blah..."
posted by still_wears_a_hat at 2:08 PM on January 1, 2019 [1 favorite]

Oops, that wasn't very clear. That last lyric is from Yazbek's The Band's Visit, but there are a lot of interesting and good lyrics in both his musicals and his 4 albums of rock/pop songs.
posted by still_wears_a_hat at 2:17 PM on January 1, 2019

The song Sing Monica, by Phish, is filled with fun wordplay.

You lift me up, you hired me
and light my day, you fired me
But then you stole the sun, delighted me
Now the day is gone, you knighted me

They have a lot of other songs with clever lyrics.
posted by bondcliff at 4:01 PM on January 1, 2019

In line with Blackalicious Alphabet Aerobics is their Chemical Calisthenics.
posted by quinndexter at 4:28 PM on January 1, 2019

My first thought was Elvis Costello so I’m glad to see he’s been named here around ten times. See (hear) his song “New Amsterdam”—

New Amsterdam it's become much too much
Till I have the possession of everything she touches
Till I step on the brakes to get out of her clutches
Till I speak double dutch to a real double duchess

posted by ejs at 6:05 PM on January 1, 2019 [1 favorite]

My current obsession is The Mountain Goats’ Tallahassee. It’s ostensibly the story of a failing marriage and the emotional ups and downs are intense. There are multiple types of music on the album which contributes to the moods of the album.

No Children is one of the best songs, but you can find the rest of the music on YouTube.

Lyrics and liner notes
posted by bendy at 6:57 PM on January 1, 2019

Also Nick Cave is an amazing wordsmith. Start with Dig Lazarus Dig.

posted by bendy at 7:38 PM on January 1, 2019

Tim Minchin might be another good example. He did the Matilda musical. See what you think about If I Didn't Have You
posted by cameradv at 7:51 PM on January 1, 2019

I'm frankly shocked Aesop Rock hasn't come up in this thread yet!
posted by potrzebie at 8:30 PM on January 1, 2019 [1 favorite]

I'm a big fan of a Christian new wave artist from the 80s named Steve Taylor, but you... certainly might not be. With that in mind, I thought I'd pull this from "Jung and the Restless," which has tickled me since I first heard it:

First came stats pulling habits out of rats
Now they may need more attention

Also this song he wrote for the newsboys, a big CCM act ca 1996: Take Me To Your Leader

Isabelle is a belly dancer
With a kleptomaniac's restraint
Tried stealing Helena's hand basket, made a fast getaway,
But McQueen she ain't

posted by Polycarp at 8:48 PM on January 1, 2019

I watched Mary poppins recently for the first time in a while, and felt this way about several of the songs , esp of course supercalifragilistic...
posted by leslievictoria at 8:57 PM on January 1, 2019


Can't link at the moment, but seriously, Shriekback.
posted by inexorably_forward at 11:03 PM on January 1, 2019

Aimee Man! "Guys Like Me" is a favorite.

'Cause guys like me, we look good at the gate
But you'll agree with the odds on the slate
And put your money on a bona fide heavyweight
And take it off guys like me, take it off guys like me
They'll pull you close but never really
Looking warm but feeling chilly
You'll describe us as impassioned
When it's just a front we've fashioned

Other artists off the top of my head: Dessa, Sara Bareilles,
Seconding artists mentioned here: Rufus Wainwright, Dar Williams, Warren Zevon, Tom Lehrer.

Breeze Brewin - General Lee — was the basis for a This American Life episode segment.
posted by nicebookrack at 11:49 PM on January 1, 2019 [1 favorite]

Also I freaking LOVE the silly Shakespearean wordplay in "Mademoiselle Juliette" by Alizée, even though I don't speak French.
posted by nicebookrack at 11:59 PM on January 1, 2019

Stephen Sondheim
Tom Lehrer
Paul Simon
Elvis Costello
Leonard Cohen
John Darnielle (The Mountain Goats)
Uncle Bonsai (Andrew Rashtin and two women)/Electric Bonsai Orchestra (Andrew Rashtin)

And Weird Al Yankovic, who is possibly the most underrated lyricist in history.

You could spend your life taking Sondheim's lyrics apart and never be done finding new cleverness. Start with the horrific pun-fest that is Sweeney Todd's Act I Finale, "A Little Priest," and you're off.

Two of my favorite lyrical passages (in an endless list of favorites) are from two songs that were written for the same character at the same moment in Follies--just at different times in the progression of the history of the musical: "The Story of Lucy and Jessie" and "Ah, But Underneath."

From "Story of Lucy and Jessie"

Lucy is juicy but terribly drab!
Jessie is dressy but cold as a slab.
Lucy wants to be dressy, Jessie wants to be juicy,
Lucy wants to be Jessie, and Jessie, Lucy -- you see
Jessie is racy but hard as a rock.
Lucy is lacy but dull as a smock.
Jessie wants to be lacy, Lucy wants to be Jessie
That's the sorrowful précis--it's very messy!

From "Ah, But Underneath"

In the depths of her interior
were fears she was inferior
or something even eerier
but no one dared to query her superior exterior

Then there's this Scandy ditty: "The Sun Won't Set" from A Little Night Music:

The vespers ring
the nightingale's waiting to sing
the rest of us wait on a string.
Perpetual sunset
is rather an unsettling thing.

The sun won't set
it's fruitless to hope or to fret
it's dark as it's going to get.
The hands on the clock turn
but don't sing a nocturne just yet.

Two artists I don't see here are Susan Werner and David Zippel. Werner is a singer-songwriter folk/soul/gospel/pop the list goes on and on, with quite a catalog and a real way with words. To feed your love of extended metaphor, may I present Misery & Happiness:

Misery sings at the Hilton
steps into the purple spotlight, leans into the microphone
Sways his hips and smooths his hair back
winks at you and gets you thinking he's handsome from a certain angle

Slips in and takes a seat
at a table in the corner and watches you with real concern
Walks up and taps your shoulder and says
"Call me when you wanna come back home."

She also wrote lyrics that I think are the two most perfect sentences about love:

There are loves that you wear
in a ring on your hand--
in a frame on your living-room shelf.
There are some that you sing
to the wide-open plain,
there are some that you keep to yourself.

David Zippel is a terrifically talented musical lyricist - he's more likely familiar as the lyricist for Disney's Hercules and Mulan, but one of the best lyric sets on Broadway in the 1980s was City of Angels, his collaboration with Cy Coleman. His lyrics are overflowing with sharp, sly wit. It's a difficult show to mount, and so doesn't get revivals (or high-school productions) as often as other musicals do. I encourage you (and anyone who loves musical theater) to seek out the score. Imagine an author singing a duet with the lead character in his detective novels:

You're nothing without me!
A no-one who'd go undefined!
You wouldn't exist
You'd never be missed
(Author:) I tell you, you're out of my mind!
A show-off! A blow-hard!
You're equal parts hot air and gall --
and no one would doubt me
without me, you're nothing at all!

inexorably_forward: Shriekback!

Can't link at the moment, but seriously, Shriekback.


posted by tzikeh at 12:01 AM on January 2, 2019 [1 favorite]

Hip hop filter: Daniel Dumile records as MF Doom / Viktor Vaughan / King Geedorah / Madvillain / etc.

You could listen to one of his songs on loop for a day and still not disentangle all the incredibleness he packs in.
posted by ZipRibbons at 3:09 AM on January 2, 2019

Do songs that are written for comedy count?

Mystery by Hugh Laurie

I live in a houseboat on an estuary
Which is handy for my work with the Thames Water Authority
But I know that you would have found it insanitry

Full lyrics
posted by lioness at 4:25 AM on January 2, 2019

Am I really the first here to mention Joni Mitchell, queen of the complex lyric? Here's one random example I'm using only because it springs to mind first: the song "Conversation."
Here's the first stanza.

He comes for conversation
I comfort him sometimes
Comfort and consultation
He knows that's what he'll find

But on my millionth listen to this song, I'm still blown away by the rhymes below (all in bold):

She speaks in sorry sentences
Miraculous repentances
I don't believe her

Tomorrow he will come to me
And he'll speak his sorrow endlessly and ask me why
Why can't I leave her?

Joni is full of poetry -- I recommend exploring her work.
(And great question, by the way.)
posted by nantucket at 4:49 AM on January 2, 2019

Oh yeah, I don't know if it's clever or more of a stunt, but Michael Clem (of Eddie From Ohio) has a song about the town with the longest name*, where he not only uses the town name, but manages to rhyme with it as well.

Michael Clem: Going Back to Llanfairpwllgwyngyllgogerychwyrndrobwllllantysiliogogogoch


*there may actually be a longer town name in New Zealand
posted by bondcliff at 8:35 AM on January 2, 2019

Many of what I came to rec are already here, but I can add:

The Tragically Hip - they do some really fun things with lyrics. I am especially fond of the way that they like to use lines that are homophones or nearly homophones, or use the same words to mean different things in the same songs. ("the Newfoundland's paws" becomes "Newfoundland paused", that sort of thing.)

Dessa - lots of cool metaphor and turns of phrase.

Anger is just love left out and gone to vinegar
you wake up a stranger to yourself
then you learn to live with her,
sit in her clothing til you fill out her figure
you know life's no bella telenovela
the tightrope bows with your weight in the center
the slide show don't put all the pictures together
you try to do it right though
(from "That Old Crow")

Janelle Monae has some really great lyrical work, especially on Dirty Computer.
posted by oblique red at 9:23 AM on January 2, 2019 [1 favorite]

Springsteen’s earliest records where he was trying to one-up Dylan on wordplay and patter come to mind. Songs like “Hard to be a saint in the city,” for example:

I had skin like leather and the diamond-hard look of a cobra
I was born blue and weathered but I burst just like a supernova
I could walk like Brando right into the sun
Then dance just like a Casanova
With my blackjack and jacket and hair slicked sweet
Silver star studs on my duds like a Harley in heat
When I strut down the street I could feel it's heartbeat
The sisters fell back and said "Don't that man look pretty"
The cripple on the corner cried out "Nickels for your pity"
Them gasoline boys downtown sure talk gritty
It's so hard to be a saint in the city
I was the king if the alley, mama I could talk some trash
I was the prince of the paupers crowned downtown at the beggar's bash
I was the pimp's main prophet I kept everythning cool
Just a backstreet gambler with the luck to lose
And when the heat came down it was left on the ground
The devil appeared like Jesus through the steam in the street
Showin' me a hand I knew even the cops couldn't beat
I felt his hot breath on my neck as I dove into the heat
It's so hard to be a saint when you're just a boy out on the street
And the sages of the subway sit just like the living dead
As the tracks clack out the rhythm their eyes fixed straightahead
They ride the line of balance and hold on by just a thread
But it's too hot in these tunnels you can get hit up by the heat
You get up to get out at your next stop but they push you
Back down in your seat
Your heart starts beatin' faster as you struggle to your feet
You're outa that hole and back up on the street
And them South Side sisters sure look pretty
The cripple on the corner cries out "Nickels for your pity"
And them downtown boys they sure talk gritty
It's so hard to be a saint in the city

posted by spitbull at 1:00 PM on January 2, 2019 [2 favorites]

Flipping through the old Jazz Fakebook... let's see...

Your Feet's Too Big - "Your pedal extremities are colossal / To me you look just like a fossil / You got me walking, talking and a-squawking / 'Cause your feet's too big"

Mack the Knife, as recreated on the fly by Ella Fitzgerald when she forgot the lyrics. "So, you've heard it, yes, we've swung it / And we tried to, yes, we sung it / You won't recognize it, it's a surprise it / This tune, called Mack the Knife"

From the same concert, Cole Porter's Too Darn Hot - "According to the Kinsey Report / Every average man you know / Prefers his lovey-dovey to court when the temperature is low / But when the thermometer goes way up / And the temperature is hot / Mr. Pants for romance is not"

In fact, you might enjoy the whole of "Ella in Berlin".

Twisted - "My analyst told me / that I was right out of my head / The way he described it / he said I'd be better dead than alive / I didn't listen to his jive"

Let's Call the Whole Thing Off - "Potato / potahto / Tomato / tomahto"

My Internet time is almost through for the day. I'll try to find some more for tomorrow.
posted by clawsoon at 5:08 PM on January 2, 2019

Regina Spektor
Death Cab for Cutie (or any Ben Gibbard stuff like Postal Service too)
+1 for Mountain Goats
posted by carlypennylane at 11:45 PM on January 2, 2019

More from the old Jazz Fakebook. I notice that most of these recordings have a slow beat; I assume that's so the average person has enough time to appreciate the wordplay.

Bewitched - Lorenz Hart - "I'm wild again, beguiled again / A simpering, whimpering child again / Bewitched, bothered and bewildered / Am I"

Imagination - Johnny Burke - "Imagination is crazy / Your whole perspective gets hazy / starts you asking a daisy / What to do"

Polka Dots and Moonbeams - Johnny Burke - "The music started and was I the perplexed one / I held my breath and said, 'May I have the next one?'"

Peel Me a Grape - David Frishberg - "You gotta wine me and dine me / Don't try to fool me, bejewel me / Either amuse me or lose me"

Love for Sale - Cole Porter - "Love that's fresh and still unspoiled / Love that's only slightly soiled"

The Joint is Jumpin - Andy Razaf and J.C. Johnson - "Get your pig feet, beer and gin / there's plenty in the kitchen / Who is that that just walked in? / Just look at the way he's twitchin'"

I Can't Get Started - Ira Gershwin - "The leading tailors follow my styles / And toothpaste ads all feature my smiles / The Astorbilts I visit, but say, what is it / With you?"

Fly Me To The Moon - Bart Howard - "Fly me to the moon and let me play among the stars / Let me see what spring is like on Jupiter and Mars"

I'm Gonna Sit Right Down and Write Myself a Letter - Joe Young - "I'm gonna write words oh so sweet / They're gonna knock me off my feet / A lotta kisses at the bottom / I'll be glad I got 'em"

Honeysuckle Rose - Andy Razaf - "Every honey bee / filled with jealousy / When they see you out with me"

And one of the great lyrics, from one of the great lyricists:

Let's Do It - Cole Porter - "Birds do it / Bees do it / Even educated fleas do it"


Lyricists who I thought would have more clever stuff but didn't quite seem to fit the bill: Oscar Hammerstein II, Johnny Mercer, Billy Strayhorn. Maybe an honourable mention for Mercer and Strayhorn (and Duke Ellington) for Satin Doll - "Baby shall we go / out skippin' / Careful amigo / you're flippin' / Speaks latin / that satin doll".

I notice that I've featured Ella Fitzgerald and Fats Waller multiple times as performers. Of the golden age jazz performers, they were the most drawn to clever lyrics and inventive ideas. Sometimes their playfulness would land them in silly novelty, but I think that's true now and then of most performers who aren't content with conventional love songs.
posted by clawsoon at 5:18 AM on January 3, 2019

Jason Mraz? Is it Wordplay that you're looking for?

I built a bridge across the stream of consciousness
It always seems to be a flowin'

(And Tim Minchin! OMG, thank you!!!!)
posted by BlueHorse at 9:49 AM on January 3, 2019

Iron and Wine has a few literate, wordy songs: The Trapeze Swinger: "But please remember me, fondly / I heard from someone you're still pretty / And then they went on to say that the Pearly Gates / Had some eloquent graffiti..." (And more.)

Josh Ritter, too: Getting Ready to Get Down: "Mama got a look at you and got a little worried / Papa got a look at you and got a little worried / Pastor got a look and said, 'Ya'll had better hurry' / Send her off to a little Bible college in Missouri..." (And more.)
posted by booth at 10:51 AM on January 3, 2019 [1 favorite]

Fiona Apple!

Fiona Apple - Extraordinary Machine
posted by bananana at 11:00 AM on January 3, 2019

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