Photo courtesy the artist
Across a four-decade-long career, Bobby Caldwell has been many things: a blue-eyed R&B singer so soulful that black audiences couldn’t believe he was white, a master of adult contemporary whose Japanese fans know him simply as “Mr. AOR” and a Frank Sinatra stand-in so convincing he’s played Ol’ Blue Eyes in Rat Pack tributes. His most enduring contribution remains 1978’s breakthrough single “What You Won’t Do for Love,” covered by Roy Ayers, Boyz II Men and Michael Bolton and sampled by 2Pac and Mariah Carey, among many, many others. Caldwell, whose most recent release was 2015’s “Cool Uncle,” made with Los Angeles producer Jack Splash, plays the newly renamed Richmond Jazz and Music Festival on Aug. 10.
Richmond magazine: People are perpetually “discovering” that you’re white. That’s been a trending topic on Twitter a few times. Were there any particularly memorable moments when people caught on?
Caldwell: I was in an elevator once,and a guy said, “Thanks a lot, Bobby, I just lost a bet.” Apparently, he bet a lot of money that I was black, and he was wrong.
RM: I understand you were friends with Bob Marley.
Caldwell: Yes, I knew Bob. It just so happens that my mother, who was a real estate broker in Florida, sold him a home. We hung out a lot — mostly things centered around music. I was already a fan.
RM: Is that how you ended up making [1980s reggae-influenced] “Jamaica”?
Caldwell: He was the catalyst for that song. I don’t know if I really got it right. Through knowing Bob, I had a feeling that I actually had been there when, indeed, I hadn’t. I still never have.
RM: I’d have figured that song alone would have gotten you some Jamaican bookings.
Caldwell: I’ll tell you what, we did send that song to the Jamaica Tourist Board.
RM: And what was their response?
Caldwell: There was none.
RM: You’ve had some distinctive eras in your career, going from R&B to diving into the American songbook.
Caldwell: It’s always a work in progress, man. It never stops. That’s how I’ve approached my career. I was R&B first. The No. 1 influence for me was Earth, Wind & Fire. But in the household I grew up in, it was Ella Fitzgerald and Frank Sinatra. I was bludgeoned with those songs my entire youth. It made an impression.
RM: You wore fedoras on the covers of a lot of your early albums and named your sophomore LP "Cat in the Hat." So where does Bobby Caldwell get his headwear?
Caldwell: There’s a girl in New York called Marsha Akins, and that’s where those hats all came from. But I don’t wear many hats anymore. I had to stop because everyone else was wearing hats.
Bobby Caldwell performs at Maymont for the Richmond Jazz and Music Festival on Aug. 10. $45 to $140.
