For much of his four-decade recording career, the soulful Bobby Caldwell, who died at his New Jersey home March 14 at the age of 71 after years of battling complications from a reaction to antibiotics, served as an unlikely rite of passage for Black music fans. Since the release of his commercial breakthrough, the 1978 R&B gem “What You Won’t Do for Love,” there continues to be no shortage of folks baffled by the revelation that the smooth crooner was white.
A cursory run-through online will lead you to myriad Internet posts and videos of surprised listeners. “After 34 years I’m just finding out that the man that sings ‘What You Won’t Do For Love’ is white,” comedian and actor Kevin Fredericks famously mused in 2018 on his popular social media series KevOnStage, perfectly summing up Black America’s astonishment while watching the barebones, pre-MTV music video of a long-haired Caldwell performing his original composition.
It’s the sort of reaction Caldwell encountered earlier during his first national tour as a solo artist, opening for Natalie Cole as his debut single began rising up the soul and pop charts. As he did throughout his life, the performer looked back at the baffled response he received with a grounded sense of humor.
“It’s the very first night in Cleveland, at an amphitheater,” Caldwell recalled in a 2015 interview with the Red Bull Music Academy. “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 f— 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.”
Of course, shock value is not enough to turn an artist into a beloved figure. Caldwell had the goods. And like fellow soulful white artists — “Sara Smile”-era Hall & Oates, the ’hood-stamped Teena Marie, British import Lisa Stansfield, 1990s R&B heartthrob Jon B and former teen star turned indie darling JoJo — Caldwell was essentially too “Black” to be fully embraced by a white pop crowd.
Caldwell was destined for the stage. His parents hosted a TV music variety program entitled Suppertime, and at 17 Caldwell was already a professional performer. He later played guitar in rock & roll pioneer Little Richard’s band. The mid-1970s, however, was a lean period for the artist, who scuffled in bar bands in Los Angeles and was rejected by a string of record labels.
By 1977, Caldwell was 27 and ready to throw in the towel and go to work for his mother Carolyn Caldwell’s real estate business in his hometown of Miami. (Her clientele included, most notably, reggae singer Bob Marley, who befriended Caldwell.) But his mother suggested he show some of his material to burgeoning local R&B powerhouse TK Records, home of George McCrae, KC & The Sunshine Band, and Betty Wright, among others, his luck changed.
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With disco on the decline, TK Records’ head Harry Stone was looking for a change and Caldwell was it. Caldwell signed a recording deal and quickly went to work on his eponymous 1978 debut album.
Yet Stone believed the finished statement was missing a lead single. Caldwell quickly composed iconic opening line of “What You Won’t Do for Love”: “I guess you wonder where I’ve been.” With its sensual Fender Rhodes keyboard and horn phrasings, the song would become his calling card, landing him both at No. 9 on the Billboard Hot 100 and No. 6 on the Hot Selling Soul chart.
The gliding “What You Won’t Do for Love” has since been covered by everyone from Cole and Peabo Bryson, Phyllis Hyman and Roy Ayers to Goldie, Boyz II Men and Jessie Ware, and prominently sampled on the posthumous 1998 Tupac Shakur hit “Do For Love.
For the suits at TK Records, Caldwell’s sound was perfect for the African American program directors who broke many of the label’s national hits. But there was one problem: Caldwell did not look the part of an R&B headliner. Stone and others were concerned that their Black fan base would laugh their white act out the room.
Yet, contrary to urban folklore, it wasn’t TK Records’ idea to feature a shadowy image of Caldwell sitting on a park bench for the cover of his LP, a marketing ploy labels often used during the 1950s and 1960s to hide the identity of Black artists from white record buyers. “It was me who came up with the idea of a silhouette, which I actually drew, based on a photo that had been taken,” Caldwell said. “I had a piece of acetate. There was a photo of me on a bench, I traced the photograph and filled it all in to make it silhouette. Everyone just loved it – problem solved and we were able to make the release in time.”
“What You Won’t do For Love” was fully embraced by Black radio’s “slow jam” format. By his second album, the criminally underrated Cat in the Hat (1980), the identity of the dapper, white guy in a hat was out of the bag. The uplifting “Open Your Eyes” became another go-to cut and would later be sampled by hip-hop visionary J Dilla for Common’s Grammy-nominated 2000 hit “The Light.” (Yes, those are Caldwell’s buttery rich vocals on the hook.)
Soon others were digging in the crates to uncover more Caldwell gems. Producer Clark Kent mined the dreamy “My Flame” for The Notorious B.I.G.’s “Sky’s the Limit,” a single that took on a somber tone with the hip-hop giant’s tragic death.
John Legend covered “Open Your Eyes” in 2013. Hip-hop group Little Brother sampled the classic for its 2019 track “Sittin Alone.” In 2016, U.K. R&B singer Ella Mai sampled “My Flame” for her song “One Day.” And five years later, Snoh Aalegra released a remake of “What You Won’t Do For Love.”
Still, Caldwell relished jumping out of the box.
His Caribbean-infused “Jamaica” (1982) could have been mistaken for the much parodied Yacht Rock sound of the 1970s and early 1980s. But Caldwell was really giving a nod to Stevie Wonder’s blissfully elegant “Rocket Love.” He co-wrote the chart-topping 1986 pop ballad “Next Time I Fall” for Chicago’s Peter Cetera and Amy Grant. In the 1990s, Caldwell drew inspiration from the Great American songbook, recording standards made famous by his childhood heroes Frank Sinatra and Nat King Cole. And in 2015, he formed the genre-merging duo Cool Uncle with Grammy-winning music producer Jack Splash (who worked with Jennifer Hudson, Alicia Keys and Kendrick Lamar).
Even after his death, followers of the artist continued to embrace that authenticity. “What y’all cookin for Bobby Caldwell’s repast?” a fan asked on Twitter, a heartfelt nod to the tradition of bringing food to a gathering following the death of a loved one. “I got the greens and pound cake.”
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