Peter J. Kaplan
3 min readApr 10, 2023

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BOBBY CALDWELL

Bobby Caldwell… “What You Won’t Do For Love”…

People of a certain age and musical taste or affinity remember that mega-hit.

I know I do.

This hit single became the signature song from his double platinum album, Bobby Caldwell, in 1978.

“What You Won’t Do For Love” (WYWDFL) reached the top ten on the Billboard Magazine Hot 100 (№9); R&B (№6); and Adult Contemporary (№10) charts.

The song has been covered, remade and sampled countless times.

Eighteen years later, Caldwell remade it himself.

Genres were crossed.

Indelibly.

Go West, Phyllis Hyman, Roy Ayers, Michael Bolton, Intro, Boys II Men and Snoh Aalegra.

Sampled by Tupac Shakur for his hit “Do It For Love.”

Perhaps Nels Abbey writing for The Guardian expressed it best when he declared,

“A Black person growing up in the west will experience moments of shock.

There is the first time you knowingly experience racism, and here for me was another:

The first time I realised that the man who sang the soul classic What You Won’t Do For Love was white.

Bobby Caldwell was white.

Blue-eyed Bobby Caldwell died on March 14.

He was 71.

Full disclosure: I never knew that Bobby Caldwell was white either.

He was not an engine of cultural appropriation…far from it.

He cut his teeth with Little Richard.

And when he made his own demo tape, the major labels roundly rejected it.

His mother had a suggestion.

Approach Henry Stone’s TK Records, a Miami-based independent powerhouse.

Think genre-defining hits such as Rock Your Baby by George McCrae, Anita Ward’s Ring My Bell or countless recordings by KC and the Sunshine Band.

Bingo!

Boom!!

His self-titled debut album was the definition of a soul record.

It sounded like he was a member of the Temptations.

Or the Stylistics.

He looked like one of the Osmonds.

Not good for R&B radio or sales.

Never a picture of Caldwell on the debut album cover.

It worked.

But when Caldwell was invited on tour by Natalie Cole, the gloves–-and the mask–had to be tossed aside.

Here’s how he remembered it:

“It’s the very first night in Cleveland, at an amphitheatre.

We’re talking about 7,000 brothers and sisters, and I was the only cracker there.

And everyone is coming to hear ‘soul brother’ Bobby Caldwell.

I walked out on stage and you could hear a pin drop, just a total hush came over the crowd.

It was like, ‘What the fuck is this!?’

I stayed and delivered, after about 10 minutes, I had them in my pocket.

That was the night I became a man, I’ll tell ya.”

Caldwell didn’t think he sounded Black (he thought he sounded “like a white guy that was influenced by R&B music,” adding, “but people would swear up and down I was Black.

Huge amounts of money were lost in bets.”).

Genuinely skilled and a heartfelt cultural practitioner of the art and its creators, Bobby Caldwell was a great soul man.

His work was immortalized for a younger generation when it was sampled by the likes of rappers (the aforementioned) Tupac, The Notorious BIG and Common.

His core audience remained Black, though he was also big in Japan.

Bobby Caldwell was extraordinarily gifted and uniquely himself.

Never judge a book–or an album–by its cover.

[Editor’s Note: This piece was written by Mr. Kaplan in April 2023.]

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