If I Lose - The Stanley Brothers & the Clinch Mountain Boys

If I Lose - The Stanley Brothers

2:08

single, 1961

Written by Ralph Stanley

Few songs look upon the gambling life with rosy optimism, but this droll bluegrass proves it can be done.  In it, the narrator begs his lady love to come back to him — not because he can't live without her, but because she has the deep pockets to bankroll his losses.  "If I lose a hundred dollars while I'm trying to win a dime / My baby she's got money all the time," he boasts.  He doesn't look at other girls; they don't have enough dough.  He's gambled all over town and lost every time, but "now that you're back dear, let's take another round."  Over some virtuoso banjo picking and a bright fiddle, and accompanied by some down home harmonies, Stanley belts out the lines with his nasal yelp.

If I Can Dream - Elvis Presley

If I Can Dream - Elvis Presley
3:09
Elvis, 1968
Written by Walter Earl Brown

This song was based on Martin Luther King's famous "I Have a Dream" speech and its passionate rendition by Elvis was partly inspired by King's assassination just two months earlier.  "If I can dream of a better land, where all my brothers walk hand in hand / Tell me why, oh why, oh why can't my dream come true?"  Presley delivers it like a man singing for redemption, his voice straining against the lush orchestration and gospel-style backing vocals.   The arrangement swells from quiet reflection — it bemoans a world "troubled by pain," shadowed by dark clouds — to an impassioned crescendo, mirroring the ache and aspiration in the lyrics.  It is said that Elvis never channeled so much grief and yearning into a song, and that after he recorded it, vowed he would never again sing a song he didn't believe in.

If Ever I Stray - Frank Turner

If Ever I Stray - Frank Turner

2:54

England Keep My Bones, 2011

Written by Frank Turner and Nigel Powell

In this rousing rocker, found on what I believe to be Turner's best album, Turner notes how life can kick us around and make things look unremittingly bleak, and that's when you're liable to call it quits: "When you've lost the fight, yeah, you've lost that hunger / To pull yourself through the day."  But then, he implores an unseen entity — maybe the invisible hand of friends and family in solidarity — to slap him around a bit if he ever loses faith.  Throw him in the English Channel until he sobers up and remembers his main tenet of life: "As long as I've got me a place to sleep / Clothes on my back and some food to eat / Then I can't ask for anything more." A psalm for the downtrodden and folk-rockin'.

I Don't Care If the Sun Don't Shine - Dean Martin

I Don't Care If the Sun Don't Shine - Dean Martin
1:57
single, 1950
Written by Mack David, 1949

This is a funny, playful song about how the narrator prefers the night time because that's when he gets to smooch his baby.  "I don't care if the sun don't shine / I get my loving in the evening time when I'm / With my baby."  It's a perfect song for Dean's carefree, swinging pubic persona.  His smooth, easy croon blends nicely with the big band and Dixie horns.  Fun fact: this song was written for the film Cinderella, but wasn't used in it.  Which makes sense, because it's just a shade risqué and doesn't really fit with the Disneyfied fairy tale tone of the film.

If It Don't Bleed - James McMurtry

If It Don't Bleed - James McMurtry

3:50

The Horses And the Hounds, 2021

Written by James McMurtry

McMurtry, son of the fabled novelist Larry McMurtry, is a master songwriter with his father's gift for vivid description and pathos. Here, he approaches aging with wry acceptance and dry humor. The narrator is a man who's lived hard and now faces his own decline: “I burned a lot of bridges and I dropped a lot of balls / It’s a wonder I can ever go back to any place I've been," he sings in a craggy deadpan. "Now it’s all I can do just to get out of bed / There's more in the mirror than there is up ahead." McMurtry's voice is limited in range, but he's cultivated a barbed deadpan delivery that cuts straight through the sentimentality other writers might lean on.  But it's not just in voice that he's similar to Bob Dylan, but his writing chops.  In this song, the keen observations, alternately droll and poignant, just flow on, one after the other.

Bulldog Skin - Guided By Voices

Bulldog Skin - Guided By Voices

3:00

Mag Earwhig!, 1997

Written by Robert Pollard

A song abut being tough on the outside, not letting the bastards grind you down.  "I crashed my nerve / I made it swerve / I made it back, was no big deal."  There's an off-key swagger to this rousing rocker, a sort of Guided by Stones going on.  Like a lot of GvB, it's abstruse and abrupt, in a way that in the hands of other bands might seem like a toss-off, but it has an infectious, lurching energy.

By the Spoonful - J.D. Short

By the Spoonful - J.D. Short

3:49

single, 1940??

Written by J.D. Short

I've never heard of him, but Short made records with Son House and Big Joe Williams, so he's the real deal.  (Also making him the real deal: a feud with another musician in which Short stabbed him and he shot Short's testicles off.)  This rollicking blues is a declaration of serious addiction, probably to a drug, but I guess it could metaphorically be about a loved one ("hit it all night long" could easily fit either interpretation).  But this guy, he'd kill his parents for a taste.  "It's all I crave, sugar, my babe, just a spoonful, spoonful / It's all I crave, sugar, my babe, carry me to my grave."  It's a catchy delta blues shuffle that picks up steam as it goes along, harmonica occasionally punctuating Short's vibrato-inflected voice.  I can only guess at the year released, information online on Short being scanty at best.

Big Idea - Ages And Ages

Big Idea - Ages And Ages

3:30

Divisionary, 2014

Written by Ages and Ages

This is a catchy singalong with handclaps and harmonies, a sort of secular chorale in the vein of The Polyphonic Spree.  The lyrics even have a similar sort of neo-hippie New Age optimism.  "All of my ins are on the outside / And I want you all to notice / 'Cause I have no will to hide."  It ends with triumphant voices over swelling piano lines.  This kind of Northwest feel-good indie warms the soul.

Burgundy Cars - Horace Greene

Burgundy Cars - Horace Greene

3:03

Early American Ice Cream, 2016

Written by Horace Greene

I don't know anything about this Wisconsin band, but I like the retro-ad vibe of their album cover.  They're billed as indie rock, but this particular song is a slinky groove, sliding around slick '70s funk riffs.  The lyrics contrast kids "with their burgundy cars and blacked-out windows down" with working people who pump gas and roam dangerous streets.  "Now the sun says sweat, and that's all he knows how to do / Work the finger 'til the bone shines through."

Betty And Dupree - Tia Blake

Betty And Dupree - Tia Blake

3:29

Folksongs And Ballads, 1971

Attributed to Blind Andrew Jenkins, 1925

This song's album was originally released only in France and sold very little, but was reissued in 2011 and rediscovered by a new generation.  The events in the song, a crime ballad, are based on a century-old true story.  On December 15, 1921, Frank DuPre robbed a jewelry store in Atlanta of an impressive diamond ring, which he gifted to his new girlfriend Betty Andrews. After evading the police for a few weeks, he got caught and was hanged the next year.  The press made a big deal of Betty's involvement, painting her as a gold digger who urged Frank on to larceny.  Blake's version presents a few barebones facts (including having Betty tell Frank to get her a  ring) in her sweet ethereal voice, with the last verse a failed reunion of the lovers in the "death house" reunion of the lovers, when Betty writes to the doomed man that "no one's gonna take your place."  Additional "fun" fact via Wikipedia: In 1960, during a custody dispute, Blake and her siblings were kidnapped by her CIA-employed father, who was later arrested and fled the country.  She should have written a song about that!  (I think she did write about it, in Granta.)