Ship of Fools: 5 Songs for the Fools

This week's songs are from Frank Sinatra, George Jones, the Impressions, Valerie June, and Peter Cat Recording Co.

April Fool’s Day is supposedly a day of jokes, silliness, and laughter. So why are all the songs about “fools” so sad? Surveying the songs for consideration here, I had nothing but laments and ballads exploring shame, regret, and bitterness. “Fool in the Rain,” at least sounds like it’s a good time, but the singer is slowly realizing they got dumped. Ditto for “Lovefool” by the Cardigans. “Linger” by the Cranberries? It all sounds so dreamy, but she’s begging to be dumped by a terrible partner.

With a few exceptions, songs about fools are typically sung from the first person. Calling someone else a fool would just sound mean—bragging about pulling one over on somebody doesn’t exactly lend itself to song, or it can sound patronizing. Outside of hip hop, where making a fool of someone else is de rigueur, the only one who can really pull it off is Aretha (Sorry, Paul).

What it comes down to is this: nobody wants to be the fool.

Here are 5 songs that commiserate with fools.

“The fool thinks himself to be wise, but the wise man knows himself to be a fool.” - William Shakespeare

Frank Sinatra - “I’m a Fool to Want You”

I recently found a copy of Where Are You?, Frank Sinatra and Gordon Jenkins’ sweeping album of “ballads of loneliness and longing,” at a used record store. It’s includes a number of songs Bob Dylan would go on to cover on Shadows in the Night, which is partially why the album piqued my interest. Apparently, Dylan was offered an opportunity to record in Capitol Records Studio B where Sinatra and Jenkins cut Where Are You?, so he decided to fill the room with those same songs. “I’m a Fool to Want You” is the only song on Where Are You? where Sinatra has a writing credit. He originally recorded it in 1951, during a low point in his career (he was dropped from Columbia a year later). In an interesting bit of trivia, Ray Charles provided some backing vocals on that recording. As it starts, it sounds a bit like the version from Where Are You? but the vocal performance is a bit weaker in the swells, yet it concludes with a big, melodramatic finish. Arranger Gordon Jenkins helped Sinatra revive his career, bringing him to Capitol Records. Where Are You? was among a suite of albums to help shift into more adult tastes, and Sinatra would use the concept album formula for much of the rest of his career.

The version of “I’m a Fool to Want You” on Where Are You? has an autumnal quality in the arrangement—especially the vocal performance. It leans heavily into the emotional distance from the “you” he’s singing about. It starts warm, before Frank turns cold on himself in breezy swells in the back half of the verses. Rather than end big as he did in 1951, the song quietly fades out into a cold wintry night. Listening to the two versions back to back is a perfect answer to “What can an arranger do for you?” Jenkins’ touch—reframing the song to reflect the album’s theme—makes all the difference.

George Jones - “I’m a Fool for Loving Her”

Where do we go after Frank Sinatra? Well, how about the guy Frank Sinatra called “the second best singer in the world.” There are a whole bunch of crazy stories about George Jones you can go look up on your own time—the guy lead an insane life—but you will forget all of it the second he starts singing. “I’m a Fool for Loving Her,” was recorded for 1980’s I Am What I Am, catching Jones in a brief window of sobriety. While he didn’t write the song about a tragic love triangle, it sounds pulled directly from Jones’ life following the dissolution of his marriage to Tammy Wynette. If I told you this was a big hit for Jones in 1980 I bet you’d take me at my word, but this is another case of absolutely incredible material being left off an official release, later added into a reissue. The song really hits its stride in the second verse. There’s not much to offer by way of musical performance or arrangement; the whole thing rests on Jones’ shoulders, and he delivers a knock out.

She doesn't really want me, but she keeps me hangin' on
I'm just someone to talk to when she's all alone
I know you keep on hoping someday she'll set me free
Well, I'm a fool for loving her, you're a fool for loving me.

The Impressions - “Fool For You”

The opening lines of “Fool For You” could fit right in with the civil rights-oriented music The Impressions are most known for:

Never liked nobody
That's been mean to me

But from thereafter, the song turns into a celebratory and ecstatic tribute to a new love. The guitar hangs on a single note for what might be the whole song, but the drums and horns sweep all over the track, punctuating Curtis Mayfield’s joyful singing about an unrequited love. It’s bright and wide awake in the verse only to lean ever so slightly into the heartache in the choruses.

“No man really becomes a fool until he stops asking questions.” - Charles Proteus Steinmetz

Valerie June ft. Carla Thomas - “Call Me A Fool”

I saw Valerie June a few years ago at a street festival, where she was performing solo. She had a style all her own, that included how she spoke in between songs. I remember “Workin’ Woman Blues” being a highlight, but given she was by herself, it sounded like a straight blues, rather than the touch of soul provided by the horns on the recording. The retro soul gets played up on “Call Me A Fool,” with that lingering tremolo guitar, late-arriving strings, and even later arriving horns to bring the song to an ascendant finish. Appropriately, June includes Stax Records legend Carla Thomas to sing back-up. But the real bright spot here is June’s distinct voice; it’s raw, a little twangy. There’s a child-like quality to a lot of her other music, but not here. They call her a fool, but she makes clear she’s not backing down.

"Never argue with fools. They will drag you down to their level and beat you with experience.” - Mark Twain

Peter Cat Recording Co. - “Foolmuse”

It’s April Fool’s Day so we’ve got to go out on a fun one, right? Peter Cat Recording Co. is a New Delhi based alt rock band, which similar to Mexico’s Cafe Tecvba, knows how to mash up and jump around different genres, sometimes within the same song. They’ve been around a while, but I’d only discovered them with 2024’s Beta, which jumps across dance music, retro soul, and acoustic rock. “Foolmuse,” falls into the charming retro soul bucket. Its a serenade from something of an unreliable narrator. Are they sweet? A little deranged? Both? Given the package they’re presenting it in, the intention can’t help but feel sweet. It’s playing a bit of a trick on the ears.

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