The Toughest Street In Town - Thin Lizzy

The Toughest Street In Town - Thin Lizzy

4:00

Black Rose: A Rock Legend, 1979

Written by Scott Gorham, Phil Lynott, and Gary Moore

One of the most punk-adjacent cuts in Thin Lizzy's catalog, this song bursts open with slashing guitars that could've come straight from the Sex Pistols (Phil Lynott's mates, and kindred spirits in attitude if not in polish).  The guitars are hard edged, Brian Downey's drumming snaps like a snare in an alley, while Lynott spits his lines with the rhythmic swagger of a boxer turned street poet. "Like a rat in a pack it attacks / From the back / Through a crack in a track / And you take a smack."  The song paints a grimy cityscape, a Lou Reed vignette refitted with power chords and defiant Irish soul. The chorus crashes in over a dependable "Louie Louie" chord, a gang chant that feels both desperate and triumphant. Then Moore detonates a furious solo, full of sharp bends and molten tone, showing he was such a natural (albeit brief) fit for Lizzy's mix of toughness and melody. 

Richest Guy In the Graveyard - Dinah Washington

Richest Guy In the Graveyard - Dinah Washington

2:52

single, 1949

Written by Frank Thurman Hedges and Louis Palmer

This charming jazz vocal number is all about carpe diem: spend your cash, die broke and happy, you can't take it with you.  Backed by the lush strings of the Teddy Stewart Orchestra, Washington swings as she delivers the funny lyrics with crisp phrasing and winking amusement.  "Now what's the good of earning / With no time for spending / You know you're simply headed / For a horizontal ending."  It's packed with playful fatalism, but Washington's delivery makes it sparkle as she delivers lines like the one about how her man won't make a great lover "Wrapped in brown / with a hardwood cover."  The big punchline, though, is at the end, when with a great crescendo of strings, Washington belts out, "So daddy won't you hear my plea / Do me a favor and please / Make out your will to me."  If he won't take her advice, Dinah plans to take his money!

The Brightest Lights - King Charles

The Brightest Lights - King Charles

3:36

LoveBlood, 2012

Written by King Charles

I've never heard of this eccentric British singer and multi-instrumentalist, but this info from Wikipedia is delightful: in 2009, he became the first British person to win the International Songwriting Competition in Nashville, Tennessee.  The judges included Tom Waits and Jerry Lee Lewis!  Now that's an accomplishment to put on your resumé.  He also released an impassioned version of "We Didn't Start the Fire" with all-new updated lyrics in 2022.  In this rousing acoustic sing-along, he's backed by Mumford & Sons, playing a folk gallop that feels like an old sea shanty or an old Irish ballad.  The lyrics are all imagery of light and shadow, twilight blotting the sun, dawn sweeping darkness away, all relating in Charles' oddball mind to hedonism and carpe diem: "Oh the moonlight shadows are fleeting and scattered / Where memories and prophecies are slain / Only the moment you're in can delight in sin / So forget your regrets and pains." It's folk-rock with a slightly deranged grin, like a Victorian poet let loose in a pub full of stompers.

The Slowest Drink at the Saddest Bar on the Snowiest Day in the Greatest City - The Lawrence Arms

The Slowest Drink at the Saddest Bar on the Snowiest Day in the Greatest City - The Lawrence Arms

3:13

Buttsweat and Tears, 2009

Written by Brendan Kelly, Chris McCaughan, and Neil Hennessy

A emo-punk song about feeling lost and alone, urban isolation, the ache of self-awareness.  The narrator wakes feeling nothing ("My eyes opened to the emptiness / My face was nothing but crooked lines / I guess somewhere I really fell behind") and trudges through the cold (Chicago?) snow to a nameless bar where no one knows him, the anti-"Cheers."  It's a universal feeling of ennui: the shower you take out of boredom, the drink you pour just to fill time.  Everything looks bleak at those moments, the soul and the weather. The narrator's grim present seems to stretch into the future.  "What will it say on my snow-covered grave? / He had it all, he let it all just slip away."

The Sharpest Thorn - Elvis Costello & Allen Toussaint

The Sharpest Thorn - Elvis Costello & Allen Toussaint

4:16

The River In Reverse, 2006

Written by Elvis Costello and Allen Toussaint

A slowburn piano ballad.  Playing on "Auld Lang Syne" ("We raise our glasses and we cheer / Should old acquaintance disappear") and invoking religious imagery ("Archangel Michael will lead the way / Archangel Gabriel is ready to play / Although we know we must repent / We hit the scene and look for sins that haven't even been invented"), Costello sings a dullard's plea earnestly over Toussaint's piano.  As the song builds to a close, drums, organ and sax strike up a New Orleans ragtime tune, bringing a bit of needed liveliness into it.

The Biggest Thing That Man Has Ever Done - Woody Guthrie

The Biggest Thing That Man Has Ever Done - Woody Guthrie

2:21

single, 1942

Written by Woody Guthrie

This anthem starts off as a tall-tale braggadocio and then gets serious.  He starts off in Year One building the Rock of Ages, picking apples in the Garden of Eden, building the pyramids and freeing the Israelites ("I opened up the ocean let the migrant children through").  Then he mentions a few historical battles, until getting to the real heart of the song: beating Adolf Hitler and the Nazis.  "We'll stop the Axis rattlesnakes and thieves of old Nippon / And that will be the biggest thing that man has ever done."  I'm sure there are other versions with different verses, and there's no way of knowing which this one is.

Let Me Play With Your Poodle - Tampa Red

Let Me Play With Your Poodle - Tampa Red

2:36

single, 1942

Written by Tampa Red (as Hudson Whittaker)

A hokum swing blues with a rollicking piano and what sounds like a kazoo.  It's surely an extended entendre for a lady part, but as with all of these early euphemistic lyrics, it can be hard to pin down.  I mean, "long black shaggy hair," I guess, sure.  Also, "And what I like about him, you keeps him clean."  But: "I like the way he twists his tail / I would buy him, but he ain't for sale."  Him?  Tail?  Anyhoo, a fun little ditty, one you might hear in a barrelhouse or bordello.

Play It Cool, Stay In School - Brenda Holloway

Play It Cool, Stay In School - Brenda Holloway 

2:29

single, 1966

Written by Jimmy Clark

A terrific Motown song with a strong R&B rhythm section and compelling lead vocals.  But was this song commissioned by Big School or something?  The lyrics are direct and literal; it's not a metaphor for anything or an anecdote.  "Cause when you learn more / You're bound to earn more / When you stay in school."  It reads like the text of a PSA.  "You'll be so thankful, so very thankful / That you decided to stay and graduate."  Thanks, mom!

Play It Cool - Alton Ellis

Play It Cool - Alton Ellis

2:39

single, 1977

Written by Alton Ellis

Another mid-tempo Rocksteady groove by Ellis.  I found one source for the year, but not much else; the original Jamaican single has almost no information.  This song is also known as "Rock On Time."  It's a laid back song about, I guess, taking it easy?  The lyrics are not exactly clear in the way rasta songs sometimes get.  "Without money I know / It really makes no difference / I've got love I know / Easy squeeze it makes no riot."  Well, that's hard to disagree with!

Don't Play That Song - Aretha Franklin

Don't Play That Song - Aretha Franklin

3:02

Spirit In the Dark, 1970

Written by Ahmet Ertegün and Betty Nelson

Obviously the narrator of this song is not as steely as Humphrey Bogart.  ("Play it, Sam!  If you can play it for her, you can play it for me. If she can take it, so can I.")  The song was co-written by Ben King's wife and released by him in 1962.  This version transforms it into a gospel-soaked soul anthem with fire and heartbreak. Her voice — soaring, pleading, utterly commanding — turns the song's simple premise into high drama: the pain of hearing a song that reminds her of a lover's lies: "I was only seventeen / I'd never dream he'd be so mean."  The arrangement blends classic Atlantic soul with churchy piano and call-and-response backing vocals that elevate the emotional stakes.