Tracks 9, 10 and 11 from Carry On (1982)

Track 12 from August Moon (1983)

Track 18 from Come Rain Or Shine (1999)

Before he was a solo star, Caldwell played in Little Richard's backing band and was good friends with Bob Marley. When he signed to TK Records, a label that released many of the biggest hits of the disco era, the label decided to promote "What You Won't Do For Love" to R&B stations and show Caldwell only as a silhouette on his album cover, letting much of the public assume he was black. And even today, it's become kind of a running joke on Twitter that every few months someone will post the "What You Won't Do For Love" video and express surprise that Caldwell is white. 

It's interesting to think about the songs by white artists that have been played heavily on R&B radio over the years. Some were by acts so famous that people were well aware of what they looked like (Elton John's "Bennie And The Jets," David Bowie's "Fame," Hall & Oates's "I Can't Go For That"), while in the '80s certain artsy pop acts were a little more deliberately faceless but it didn't feel like anyone cared too much about the race of who made it (Nu Shooz's "I Can't Wait," Art Of Noise's "Moments In Love," Tom Tom Club's "Genius Of Love"). Later in the music video age, it felt like white R&B singers like Jon B. and Robin Thicke could find a semi-comfortable niche with everyone being aware of their race a little more than in Caldwell's era. 

But then, to me Caldwell sounds mostly like a jazz/blues-influenced soft rock guy like Michael McDonald, Steely Dan, or his friend Boz Scaggs. "What You Won't Do For Love" even has a flugelhorn on it! And a lot of his music sounds like it could've been made by Chicago or one of the acts that now gets called 'yacht rock' (in fact, Caldwell wrote a #1 hit, "Next Time I Fall," for Chicago's Peter Cetera). That's not a diss, because I like all those artists, and I think we kind of lost something when guys like that disappeared from the charts. 

"Open Your Eyes," a deep cut from Caldwell's second album, was famously sampled on Common's hit "The Light." Lil Nas X's "Carry On" sampled the title track of Caldwell's Carry On, and Caldwell's publisher sued Lil Nas X for millions in 2018. Caldwell had his last Hot 100 hit in 1982 (although in 1988 he released the lead single for the soundtrack to the legendarily awful movie Mac And Me). And his commercial decline, unfortunately, had a lot to do with label woes. TK Records collapsed in the early '80s as disco declined, and Caldwell initially released August Moon only in Japan, where his albums had sold better than in America. 

It seems like Caldwell was happy to continue making music under whatever circumstances he could, experimenting with a whole range of styles, including singing a lot of standards on his later albums and even playing Frank Sinatra in a musical. But in 2015, on what would be his final album Cool Uncle, Caldwell hooked up with a younger producer, Jack Splash (Alicia Keys, Kendrick Lamar), and sang on some funky retro R&B tracks with people like Cee-Lo Green and Jessie Ware.