A Million Little Pieces Of My Mind

Artificial Intelligence

Whippoorwill Through the Decades

By: Paul S Cilwa Posted: 8/16/2026 Page Views: 278
Hashtags: #AI #Music #Suno #Whippoorwill
One song, sixteen AI-generated arrangements spanning a century of musical styles.
Estimated reading time: 4 minute(s) (757 words)

As described in more detail in the Music section, I recently started working with old song lyrics and melodies I've saved since I wrote them in the 1960s-1990s. One of those songs was Whippoorwill, with lyrics by my own mom, Edna Mae Brown-Cilwa. It was a little piece, not typical of mine, but I found myself singing it—apparently the tune was catchier than I had at first thought.

I've started playing with an A.I. music creation tool, Suno.com. For fun, I took Whippoorwill (that's also the 1973 version, below), I thought I'd see how hard it would be to change the style completely. Before I could stop myself, I'd done a version for nearly every decade of the last hundred years, and a few even earlier ones. I expected most of them to be garbage—slop, as the kids say—but to my surprise, I actually like all of them. Some more than others, but I guess you can't keep a catchy tune down!

A note on the styles: I never asked Suno for any of these by name. It refuses to imitate specific singers or groups. But those were the sounds in my head when I wrote each prompt. Below, for each decade, I'll tell you what I was going for—see how close you think the A.I. came.

1700s

Going for Baroque

I was going for Bach: a small chamber ensemble, harpsichord, tight Baroque counterpoint. See if you hear him in there.

1800s

Classical

This one's aimed at Mozart—classical-era elegance, strings and winds, that clean Viennese symmetry.

1850s

Minstrel

I wanted a Stephen Foster minstrel song—parlor piano, that plainspoken 19th-century melody. I couldn't talk the A.I. into an old-timey solo voice for this one, though; the vocal is more modern than I'd have liked.

1890s

Ragtime

Straight-up Joplin-style ragtime. Syncopated piano, that unmistakable rag lilt.

1920s

Fox trot

A jaunty dance-band swing, the sound of a Jazz Age ballroom.

1930s

Fox trot

Another fox trot, but a decade on—smoother, a little more sophisticated. See if you can hear the difference between this one and the 1920s version.

1940s

Big Band

Horns, a driving rhythm section, that wartime dance-hall energy.

1950s

Swinging Crooner

I had in mind something in the neighborhood of Bobby Darin. Judge for yourself how close it lands.

1965

British Invasion

Mop-top guitars and a Mersey beat—the sound of half the bands that got off a plane from Liverpool in 1964. See if you catch a whiff of the Fab Four in there.

1967

American Revolution

A rock group take—I was picturing something like the Association. Jangly guitars, close vocal harmonies, sunny mid-60s pop-rock.

1969

Motown

Girl-group energy—think the Supremes. Tambourine, tight harmonies, that unmistakable Detroit bounce.

1970s

Adult Contemporary

An earnest female vocal in the Carpenters' vein—soft, lush, impeccably produced.

1973

Folk

This is the one that started it all—the version I actually recorded for my new album. I was going for a Joni Mitchell feel: airy vocal, open guitar voicings, that confessional-folk quality. Everything below happened because I liked this one so much I wanted to see what else the song could become.

2000s

Boy band

Stacked harmonies, a slick pop production—the sound of a hundred teen-pop groups I couldn't tell apart at the time.

2010s

Progressive/Symphonic Rock

I wanted Emerson, Lake & Palmer—prog-rock bombast, big keyboards, orchestral flourishes. This is the most over-the-top version of the bunch, and I mean that as a compliment.

2020s

Pop Diva

Big, polished, radio-ready. A hundred years after the 1920s fox trot, and the whippoorwill is still keeping somebody up at night.