Have You Heard of Bobby Caldwell? The Soulful Singer Had Black Folks Fooled for Decades

Bobby Caldwell was born on August 15, 1951, in New York City to Bob and Carolyn Caldwell. The Caldwells, who were both entertainers, raised their son in the Miami area. Their home was filled with music, and Bobby taught himself to play the guitar and the piano.

By the time he was a teenager, Bobby was writing his own songs and in the late 1960s, he joined the Miami-based blues-rock band Katmandu as a bassist. Besides writing songs and performing with the band, Caldwell also played guitar for Little Richard’s band in the 1970s.

Caldwell eventually left the band for a solo career and signed a deal with Miami-based record label TK Records in the late 1970s. He scored his first big hit as a solo artist in 1978 with “What You Won’t Do For Love.”

TK Records’ executives told Caldwell that urban radio stations wouldn’t play his song with a white guy’s face on the album cover, so they found a creative way to keep his identity a secret.

“In a rush to fix things, I drew up this silhouette of a guy on a park bench,” Caldwell told TV ONE in an interview.

But as his song found success, Caldwell couldn’t hide forever, and he was forced to let the world in on his secret during one of his first live shows in Cleveland, Ohio.

“When I came out on stage, a hush came over the audience, like in disbelief,” he recalled. “And it was in that first 15 minutes in front of that audience that I think I became a man.”

Bobby’s debut album also featured the rhythmic ballad “My Flame.” You’ll probably recognize the melody, which was famously sampled by the late Notorious B.I.G. on his 1997 single “Sky’s the Limit,”which was featured on Biggie’s “Life After Death” album.

Caldwell released his second album, “Cat in the Hat,” via TK Records in 1980. Caldwell has writing credits on every track, including the soulful single “Open Your Eyes.” From the first note, you’ll instantly recognize the song, which was sampled on the Common 2000 hit, “The Light.”

But Caldwell didn’t keep all of his songwriting talent to himself. He also penned songs for other artists, including 1982's “Never Loved Before,” a beautiful ballad he wrote for Roberta Flack. He also wrote “All or Nothing at All,” a jazzy track he for Al Jarreau.

Caldwell continued to influence soulful singers for decades, including R&B hitmaker Eric Benét, who in an interview called Caldwell one of his biggest influences.

Everything changed for Caldwell in 2017, when he was given antibiotics to manage a runny nose and cough he had before heading to Japan to perform. A week later, Caldwell’s wife Mary said he was dealing with excruciating pain that would change his career forever, leaving him unable to stand during shows. He performed sitting behind a keyboard for the next three years, until the COVID pandemic ended his performing career for good.

“He was literally living this tortured life between the pain and the mobility,” she told Katie Couric in an interview.

Bobby Caldwell died at his home in New Jersey in 2023. He was 71. His death was attributed to an adverse reaction to an antibiotic – a condition known as being “floxed,” according to Boston 25 News.

“Bobby passed away here at home. I held him tight in my arms as he left us. I am forever heartbroken. Thanks to all of you for your many prayers over the years,” his wife Mary wrote in a March 15, 2023, post on X.

The music industry paid tribute to Caldwell after his death, including Chance The Rapper, who shared an exchange between the two on social media along with a heartwarming post.

“This never happens. I’ve never received a message from an artist thanking me for sampling their record. This is a record that hasn’t even come out, and the legend himself reached out. I was so excited to meet you, I have not felt broken like this at a strangers passing in so long. You are a true legend and incredible person who I know I will see one day,” he wrote on Instagram in March 2023.

The popularity of Caldwell’s “What You Won’t Do For Love” track got another big boost in 2024 when it was used as the soundtrack to TikTokers showing off their decadent dishes on the app. We’re pretty sure most of the posters weren’t even born when the song came out in 1978.